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Trimethylamine

PubChem CID
1146
Structure
Trimethylamine_small.png
Trimethylamine_3D_Structure.png
Molecular Formula
Synonyms
  • trimethylamine
  • N,N-dimethylmethanamine
  • 75-50-3
  • Methanamine, N,N-dimethyl-
  • N-Trimethylamine
Molecular Weight
59.11 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Trimethylamine, anhydrous appears as a colorless gas with a fishlike odor at low concentrations changing to ammonia-like odor at higher concentrations. Shipped as a liquid under its own vapor pressure. Contact with the unconfined liquid can cause frostbite from evaporative cooling or chemical type burns. The gasis corrosive and dissolves in water to form flammable, corrosive solutions. Gas is an asphyxiate by the displacement of air. Produces toxic oxides of nitrogen during combustion. Prolonged exposure to heat can cause the containers to rupture violently and rocket. Long-term inhalation of low concentrations or short -term inhalation of high concentrations has adverse health effects.
Trimethylamine, aqueous solution appears as a clear to yellow aqueous solution of a gas. Odor varies from fishlike to ammonia-like depending on vapor concentration. Flash point (25% solution) 35 °F. Corrosive to skin and eyes. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen when burned.
Trimethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an methyl group. It has a role as a human xenobiotic metabolite and an Escherichia coli metabolite. It is a tertiary amine and a member of methylamines. It is a conjugate base of a trimethylammonium.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Trimethylamine.png

1.2 3D Conformer

1.3 Crystal Structures

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-dimethylmethanamine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C3H9N/c1-4(2)3/h1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GETQZCLCWQTVFV-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CN(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C3H9N
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C3H9N

(CH3)3N

2.3 Other Identifiers

2.3.1 CAS

75-50-3

2.3.3 Deprecated CAS

4558-12-7

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 UN Number

2.3.7 ChEBI ID

2.3.8 ChEMBL ID

2.3.9 DSSTox Substance ID

2.3.10 FEMA Number

2.3.11 HMDB ID

2.3.12 ICSC Number

2.3.13 JECFA Number

1610

2.3.14 KEGG ID

2.3.15 Metabolomics Workbench ID

2.3.16 Nikkaji Number

2.3.17 NSC Number

2.3.18 Pharos Ligand ID

2.3.19 RTECS Number

2.3.20 Wikidata

2.3.21 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • HBr of trimethylamine
  • HCl of trimethylamine
  • HI of trimethylamine
  • trimethylamine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
59.11 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
59.073499291 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
59.073499291 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
3.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
4
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Trimethylamine, anhydrous appears as a colorless gas with a fishlike odor at low concentrations changing to ammonia-like odor at higher concentrations. Shipped as a liquid under its own vapor pressure. Contact with the unconfined liquid can cause frostbite from evaporative cooling or chemical type burns. The gasis corrosive and dissolves in water to form flammable, corrosive solutions. Gas is an asphyxiate by the displacement of air. Produces toxic oxides of nitrogen during combustion. Prolonged exposure to heat can cause the containers to rupture violently and rocket. Long-term inhalation of low concentrations or short -term inhalation of high concentrations has adverse health effects.
Trimethylamine, aqueous solution appears as a clear to yellow aqueous solution of a gas. Odor varies from fishlike to ammonia-like depending on vapor concentration. Flash point (25% solution) 35 °F. Corrosive to skin and eyes. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen when burned.
Gas or Vapor; Liquid; Gas or Vapor, Liquid
Colorless gas with a fishy, amine odor; Note: A liquid below 37 degrees F. Shipped as a liquefied compressed gas; [NIOSH]
Liquid
COLOURLESS COMPRESSED LIQUEFIED GAS WITH CHARACTERISTIC ODOUR.
COLOURLESS SOLUTION IN WATER WITH PUNGENT ODOUR.
Colourless gas; Pungent fishy odour at low concentration
Colorless gas with a fishy, amine odor.
Colorless gas with a fishy, amine odor. [Note: A liquid below 37 °F. Shipped as a liquefied compressed gas.]

3.2.2 Color / Form

Colorless gas at room temperature
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Colorless gas [Note: A liquid below 37 °F. Shipped as a liquefied compressed gas]
NIOSH. NIOSH Pocket Guide to Chemical Hazards. Department of Health & Human Services, Centers for Disease Control & Prevention. National Institute for Occupational Safety & Health. DHHS (NIOSH) Publication No. 2010-168 (2010). Available from: https://www.cdc.gov/niosh/npg

3.2.3 Odor

Pungent, fishy, ammoniacal
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
Fishy, amine odor
NIOSH. NIOSH Pocket Guide to Chemical Hazards. Department of Health & Human Services, Centers for Disease Control & Prevention. National Institute for Occupational Safety & Health. DHHS (NIOSH) Publication No. 2010-168 (2010). Available from: https://www.cdc.gov/niosh/npg
A fish-like odor at low concentrations changing to an ammonia-like odor at higher concentrations.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 1086

3.2.4 Taste

Old fish
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Volume 2. Boca Raton, Florida: CRC Press, Inc., 1980., p. 304
Saline taste
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799

3.2.5 Boiling Point

37.2 °F at 760 mmHg (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
37.17 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
2.87 °C at 760 mm Hg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
3 °C
30 °C
37.2 °F
37 °F

3.2.6 Melting Point

-178.8 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
-179 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
-117.08 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
-117.1 °C
-117 °C
-3 °C
-179 °F

3.2.7 Flash Point

Not Applicable. Gas. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
10 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
-7 °C (19 °F) - closed cup
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
20 °F (Closed cup)
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
10 °F (-12.2 °C) (closed cup)
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1387
25% solution: 38 °F (3.3 °C) (open cup)
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Flammable gas
-7 °C
NA (Gas) 20 °F (Liquid)

3.2.8 Solubility

48 % at 86 °F (NIOSH, 2024)
Very soluble (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
In water, 8.9X10+5 mg/L at 30 °C
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V2: 272 (1978)
Soluble in water
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Soluble in alcohol, ether
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Readily absorbed by alcohol with which it is miscible; also soluble in ether, benzene, toluene, xylene, ethylbenzene, chloroform.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
For more Solubility (Complete) data for Trimethylamine (7 total), please visit the HSDB record page.
890.0 mg/mL
Solubility in water: very good
Soluble in water, ether
Soluble (in ethanol)
(86 °F): 48%

3.2.9 Density

0.633 at 68 °F (USCG, 1999) - Less dense than water; will float
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
0.6356 (NTP, 1992) - Less dense than water; will float
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
0.6709 at 0 °C/4 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
Saturated liquid density= 40.890 lb/cu ft @ 35 °C
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
Saturated vapor density= 0.29910 lb/cu ft @ 70 °C
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
Relative density (water = 1): 0.6 (liquid)
Relative density (water = 1): 0.9
0.667-0.675 (4°)
0.633 at 68 °F
2.09(relative gas density)

3.2.10 Vapor Density

2 (USCG, 1999) - Heavier than air; will sink (Relative to Air)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
2 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
2.0 (Air = 1)
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V5: 4408
Relative vapor density (air = 1): 2
Relative vapor density (air = 1): 2.0
2.09

3.2.11 Vapor Pressure

1487.83 mmHg at 70 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
1610 mm Hg at 25 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.
Vapor pressure, kPa at 20 °C: 187
Vapor pressure, kPa at 20 °C: 67
1454 mmHg at 70 °F
(70 °F): 1454 mmHg

3.2.12 LogP

log Kow = 0.16
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 9
0.16
HANSCH,C ET AL. (1995)
0.2
-0.3

3.2.13 Henry's Law Constant

Henry's Law constant = 1.04X10-4 atm-cu m/mole at 25 °C
Christie AO, Crisp DJ; J Appl Chem 17: 11-4 (1967)

3.2.14 Stability / Shelf Life

Stable under recommended storage conditions.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).

3.2.15 Autoignition Temperature

374 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
374 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
374 °F (190 °C)
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-111
190 °C

3.2.16 Decomposition

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx).
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Products of decomposition include carbon monoxide, carbon dioxide, hydrocarbons, and toxic oxides of nitrogen as well as toxic amine vapors.
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 49-152
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577

3.2.17 Viscosity

5.1564X10-4 Pa.sec at 200 K
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

3.2.18 Corrosivity

Aqueous solutions are corrosive
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799

3.2.19 Heat of Combustion

-2443.1 kJ/mol
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 5-68

3.2.20 Heat of Vaporization

21.66 kJ/mol at 25 °C
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 6-144

3.2.21 pH

Strong base
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799

3.2.22 Surface Tension

17.4 dynes/cm at -4 °C
Flick, E.W. (ed.). Industrial Solvents Handbook 4 th ed. Noyes Data Corporation., Park Ridge, NJ., 1991., p. 710

3.2.23 Ionization Potential

7.82 eV

3.2.24 Ionization Efficiency

Ionization mode
Positive
logIE
1.81
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)
Reference

3.2.25 Odor Threshold

Odor Threshold Low: 0.0002 [ppm]

Odor Threshold High: 0.00087 [ppm]

Odor threshold from AIHA

1.70 ppm (detection in water, chemically pure)
Fazzalari, F.A. (ed.). Compilation of Odor and Taste Threshold Values Data. ASTM Data Series DS 48A (Committee E-18). Philadelphia, PA: American Society for Testing and Materials, 1978., p. 160
2.10X10-4 ppm (recognition in air, chemically pure)
Fazzalari, F.A. (ed.). Compilation of Odor and Taste Threshold Values Data. ASTM Data Series DS 48A (Committee E-18). Philadelphia, PA: American Society for Testing and Materials, 1978., p. 160
2.20X10+11 molecules/cu cm (in air, purity, not specified)
Fazzalari, F.A. (ed.). Compilation of Odor and Taste Threshold Values Data. ASTM Data Series DS 48A (Committee E-18). Philadelphia, PA: American Society for Testing and Materials, 1978., p. 160
5.00X10-4 mg/kg ppm (detection in water, other)
Fazzalari, F.A. (ed.). Compilation of Odor and Taste Threshold Values Data. ASTM Data Series DS 48A (Committee E-18). Philadelphia, PA: American Society for Testing and Materials, 1978., p. 160
For more Odor Threshold (Complete) data for Trimethylamine (7 total), please visit the HSDB record page.

3.2.26 Refractive Index

Index of refraction: 1.3631 at 0 °C/D
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-532

3.2.27 Dissociation Constants

Basic pKa
9.8
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037
pKa = 9.80 (conjugate acid)
Perrin DD; Dissociation constants of organic bases in aqueous solution. IUPAC Chem Data Ser: Suppl 1972. Buttersworth, London. (1972)

3.2.28 Kovats Retention Index

Standard non-polar
518
Semi-standard non-polar
479 , 503 , 503 , 500.4
Standard polar
553 , 609 , 609 , 570 , 570 , 576 , 546 , 554 , 561 , 570 , 610

3.2.29 Other Experimental Properties

Readily liquified
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Liquefiable by pressure at ordinary temperature or by condensation
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
Conversion units: 1 mg/L = 414 ppm; 1 ppm = 2.42 mg/cu m
Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 1090
Vapor (Gas) Specific Gravity: 2.0; Ratio of Specific Heats of Vapor (Gas): 1.139; Heat of Solution: -385 Btu/lb = -214 cal/g = -8.96X10+5 J/kg
NOAA; CAMEO Chemicals. Database of Hazardous Materials. Trimethylamine, anhydrous (75-50-3). Natl Ocean Atmos Admin, Off Resp Rest; NOAA Ocean Serv. Available from, as of Mar 7, 2018: https://cameochemicals.noaa.gov/
For more Other Experimental Properties (Complete) data for Trimethylamine (12 total), please visit the HSDB record page.
Decomposition temp: 800-1300 °C; Dielectric constant at 4 °C: 2.9; Electrical conductivity: 2.2X10-12 reciprocal ohms @ - 33.5 °C; Ionization constant at 25 °C: 6.5X10-5 for solutions 0.001-0.06N; Heat of vaporization at BP: 95.6 cal/g
Flick, E.W. (ed.). Industrial Solvents Handbook 4 th ed. Noyes Data Corporation., Park Ridge, NJ., 1991., p. 710

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Nitrogen Compounds -> Amines, Aliphatic

3.4.1 Drugs

Pharmaceuticals -> Metabolite of Levocarnitine
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043

3.4.2 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
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Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
2.89:100.00
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2 of 4
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Spectra ID
Instrument Type
JEOL
Frequency
300 MHz
Solvent
CCl4
Shifts [ppm]:Intensity
2.12:1000.00
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4.1.2 13C NMR Spectra

1 of 4
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Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
47.46:256.79, -0.00:16.61
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2 of 4
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Spectra ID
Frequency
400 MHz
Solvent
H2O
Shifts [ppm]
47.46
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4.1.3 15N NMR Spectra

Instrument Name
Bruker WH-180
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-1H NMR Spectra

2D NMR Spectra Type
1H-1H TOCSY
Spectra ID
Shifts [ppm] (F2:F1)
2.89:2.89
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4.2.2 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
2.88:47.47:1.00
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 8
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

58.0 99.99

59.0 43.57

42.0 36.49

30.0 15.51

43.0 8.70

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Notes
instrument=HITACHI M-80B
2 of 8
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80B
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

58 99.99

59 43.57

42 36.49

30 15.51

43 8.70

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License
CC BY-NC-SA

4.3.2 MS-MS

1 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

44.0492 100

42.0334 6.73

43.0414 3.48

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2 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

60.0806 100

45.0572 22.90

44.0493 11.12

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4.3.3 LC-MS

1 of 3
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MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
60.081045906016
Instrument
Agilent QTOF 6550
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
10
Top 5 Peaks

60.0806 100

45.0572 22.90

44.0493 11.12

45.0855 0.84

44.0776 0.51

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MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
60.081045906016
Instrument
Agilent QTOF 6550
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
20
Top 5 Peaks

44.0489 100

45.0571 26.87

60.0809 13.66

45.0853 1.05

60.1026 0.80

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4.3.4 Other MS

1 of 2
Other MS
MASS: 18972 (NITS/EPA/MSDC Mass Spectral database, 1990 version)
2 of 2
Authors
SODA AROMATIC CO., LTD.
Instrument
HITACHI M-80B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

58 999

59 436

42 365

30 155

43 87

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License
CC BY-NC-SA

4.4 UV Spectra

Max absorption: 161 nm (Log e = 3.4); 190.5 nm (Log e = 3.59); 227 nm (Log e = 2.95) (gas)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-110

4.5 IR Spectra

IR Spectra
IR: 9718 (Sadtler Research Laboratories Prism Collection)

4.5.1 FTIR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
Neat (KBr)
Source of Spectrum
Forensic Spectral Research
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Between salts
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
W324108
Lot Number
02619AH
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.5.2 ATR-IR Spectra

Instrument Name
PerkinElmer SpectrumTwo
Technique
ATR-IR
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
301256
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Raman Spectra

Catalog Number
243205
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
3241
GRAS Number
4
JECFA Flavor Number
1610

8.3 Associated Foods

8.4 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
TRIMETHYLAMINE
Evaluation Year
2005
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

9 Pharmacology and Biochemistry

9.1 Absorption, Distribution and Excretion

The absorption, distribution, and biotransformation of TMA ... /was/ followed in rats given intravenous doses of 1 to 2 g/kg. TMA was rapidly distributed to tissues, especially the liver. In rats, TMA was 81% available after oral administration, reached a peak blood level 1 hour after oral administration, and was cleared with a half-life of 2 to 2.5 hours. When fed a synthetic diet, clearance showed a two-fold reduction. Conversion of TMA to its metabolite, trimethylamine-N-oxide, proceeded slowly in liver homogenates. In humans, TMA is formed in the intestinal tract from dietary choline. Large doses of choline result in disproportionately higher formation and urinary excretion of TMA. In newborn dairy calves, fecal trimethylamine levels are clearly higher in milk-fed calves and show huge elevations in diarrheic cases. Although fish is a major source of TMA in the diet, strawberries, kale juice, and garlic have been shown to increase urinary TMA levels.
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2
TMA penetrated both rat and human skin readily when applied to the epidermal surface with flux rates ranging from 3.4 to 265 ug/sq cm/hour in rats and from 0.98 to 92.7 ug/sq cm/hour in humans with dose applications of 0.1, 1, and 10 mg per 0.32 sq cm skin membrane. Both rat and human skin could act as a reservoir and evidence exists for small but detectable N-oxide forming during passage through the skin.
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2
... About 50% of the dose of trimethylamine hydrochloride (administered orally to dogs) was eliminated unchanged together with traces of dimethylamine, suggesting that trimethylamine was N-dealkylated.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 713
It can be absorped through the skin and/or eye contact, inhalation, and ingestion (solution).
Sittig, M. Handbook of Toxic and Hazardous Chemicals and Carcinogens, 2002. 4th ed.Vol 1 A-H Norwich, NY: Noyes Publications, 2002., p. 2275
For more Absorption, Distribution and Excretion (Complete) data for Trimethylamine (6 total), please visit the HSDB record page.

9.2 Metabolism / Metabolites

When administered to humans, dogs, or rabbits, /trimethylamine/ is partly degraded to ammonia and subsequently to urea, and oxidized to trimethylamine oxide.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 713
The Sperber technique of infusion into the renal portal circulation in chickens was used to investigate in vivo the renal tubular transport and renal metabolism of trimethylamine (TMA). When 14C-TMA was infused at a rate of 1 x 10(-9) mol/min the transport efficiency (TE), that is, the tubular excretion of the (14)C-label relative to excretion of simultaneously infused paminohippuric acid, was 0.70. Progressive addition of unlabeled TMA up to infusion rates of 1 x 10(-5) mol/min produced a progressive fall in the TE of the (14)C-label. Identification of the (14)C-label excreted in the urine revealed that approximately 85% of the infused (14)C-TMA was excreted by the infused kidney as a single metabolite over the entire range of infusions. By use of the techniques of low-voltage electrophoresis, high-voltage electrophoretic mobility-pH profile, and gas chromatography/mass spectrometry, the renal metabolite was found to be identical with standard (14)C-trimethylamine oxide (TMAO). At a TMA infusion rate of 1.5 x 10(-6) mol/kg/min reaching the infused kidney, the rate at which TMAO was formed and excreted by the kidney was 0.12 x 10(-6) mol per g of kidney per min. When (14)C-TMAO was infused into chickens its TE was 0.11, which was not evidence for active excretory transport. Infused TMA was almost entirely metabolized in vivo to its N-oxide, TMAO, which then entered the urine. The renal tubular excretion of (14)C during infusion of (14)C-TMA was inhibited by the cationic blocker of transport, quinine, and by the anionic blocker of transport, probenecid.
Acara M et al; Drug Metab Dispos 5 (1): 82-90 (1977)
Humans ingest substantial amounts of choline and lecithin as part of common foods. Physicians have recently begun administering large doses of these compounds to individuals with neurological diseases. A significant fraction of ingested choline is destroyed by enzymes within gut bacteria, forming trimethylamine (TMA), dimethylamine (DMA) and monomethylamine (MMA). Some of these methylamines are eventually excreted into the urine, presumably after being absorbed and carried to the kidneys via the bloodstream. The methylamines formed after choline is eaten could be substrates for the formation of nitrosamines, which have marked carcinogenic activity. Twenty-seven millimoles of choline chloride, choline stearate or lecithin were administered to healthy human subjects. It was found that these treatments markedly increased the urinary excretion of TMA, DMA and MMA, with choline chloride having the greatest effect. Rats were treated with 2 mmol/kg b.wt. of choline chloride or lecithin, and it was found that these treatments significantly increased urinary TMA excretion and did not alter DMA or MMA excretion. Our choline chloride preparation contained no MMA, DMA or TMA; however, it was found that our choline stearate and all the commercially available lecithins tested were contaminated with methylamines. Prior removal of methylamines from our lecithin preparation minimized the effect of oral administration of this compound on methylamine excretion in urine of rats and humans.
Zeisel SH et al; J Pharmacol Exp Ther 225 (2): 320-4 (1983)
Flavin-containing monooxygenase form 3 (FMO3) is one of the major enzyme systems that protect humans from the potentially toxic properties of drugs and chemicals. Flavin-containing monooxygenase form 3 converts nucleophilic heteroatom-containing chemicals and endogenous materials to polar metabolites, which facilitates their elimination. For example, the tertiary amine trimethylamine is N-oxygenated by human flavin-containing monooxygenase form 3 to trimethylamine N-oxide, and trimethylamine N-oxide is excreted in a detoxication and deoderation process. In normal humans, virtually all trimethylamine is metabolized to trimethylamine N-oxide. In a few humans, trimethylamine is not efficiently metabolized to trimethylamine N-oxide, and those individuals suffer from trimethylaminuria, or fishlike odor syndrome. Previously ... mutations of the flavin-containing monooxygenase form 3 gene that cause trimethylaminuria /were identified/. /The authors/ report two prevalent polymorphisms of this gene (K158E and V257M) that modulate the activity of human monooxygenase form 3.
Cashman JR et al; Drug Metab Dispos 28 (2): 169-73 (2000)
For more Metabolism/Metabolites (Complete) data for Trimethylamine (10 total), please visit the HSDB record page.
Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

9.3 Biological Half-Life

In rats, TMA was 81% available after oral administration, reached a peak blood level 1 hour after oral administration, and was cleared with a half-life of 2 to 2.5 hours.
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2

9.4 Human Metabolite Information

9.4.1 Tissue Locations

  • Epidermis
  • Skeletal Muscle

9.5 Biochemical Reactions

9.6 Transformations

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used in organic synthesis, as an insect attractant, and as a warning gas in natural gas; [Merck Index] Also used as a flotation agent; It is a natural decomposition product of plants and animals; [ACGIH]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
Industrial Processes with risk of exposure
Metal Extraction and Refining [Category: Industry]
For trimethylamine (USEPA/OPP Pesticide Code: 211601) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's Database on Trimethylamine (75-50-3). Available from, as of February 22, 2018: https://npirspublic.ceris.purdue.edu/ppis/
Organic synthesis, especially of choline salts, warning agent for natural gas, manufacture of disinfectants, flotation agent, insect attractant, quaternary ammonium compounds, plastics.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378

Reported uses (ppm):

Table: Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994)

Food Category
Baked goods
Usual
9.88
Max.
21.04
Food Category
Condiments, relishes
Usual
0.32
Max.
1.05
Food Category
Frozen dairy
Usual
1.00
Max.
1.00
Food Category
Gelatins, puddings
Usual
1.00
Max.
1.00
Food Category
Meat products
Usual
6.62
Max.
13.99
Food Category
Nonalcoholic beverages
Usual
1.00
Max.
1.00
Food Category
Soft candy
Usual
1.00
Max.
1.00
Food Category
Snack foods
Usual
20.00
Max.
30.00

Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1936
Manufacture of pesticides, textile dyes, and photochemicals
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 2124
For more Uses (Complete) data for Trimethylamine (6 total), please visit the HSDB record page.
Naturally produced by the body (endogenous).

10.1.1 Use Classification

Food additives -> Flavoring Agents
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Hazard Classes and Categories -> Flammable - 4th degree

10.1.2 Industry Uses

  • Intermediate
  • Intermediates
  • Processing aids, specific to petroleum production

10.1.3 Consumer Uses

  • Intermediate
  • Not Known or Reasonably Ascertainable

10.2 Methods of Manufacturing

Preparation from paraformaldehyde and ammonium chloride; ... by the action of formaldehyde and formic acid on ammonia ... .
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
Interaction of methanol and ammonia over a catalyst at high temperature. The mono-, di-, and trimethylamines are produced, and yields are regulated by conditions. Method of purification: Azeotropic or extractive distillation.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Although methylamines can be prepared by a variety of methods including alkylation of ammonia with methyl halides, alkylation of ammonium chloride with methanol, hydrogenation of hydrogen cyanide, reductive amination of carbon monoxide or carbon dioxide, and addition of ammonia to dimethylether, commercial processes involve reaction of methanol with ammonia. Reactions occur in the vapor phase over one or more fixed bed reactors to form the corresponding mono-, di-, and tri-methylamines. The technology to manufacture methylamines ... involves use of a solid acid catalyst for the methanol amination reaction. An equilibrium distribution of MMA, DMA, and TMA is produced that favors TMA at low ammonia:methanol molar ratios. For example, at an ammonia:methanol molar ratio of 1, the equilibrium product composition is 17 mol% MMA, 21 mol% DMA, and 62 mol% TMA.
Roose P et al; Methylamines. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2018). John Wiley & Sons, Inc. Online Posting Date: July 15, 2011
Methylamines are prepared commercially by the exothermic reaction of methanol with ammonia over an amorphous silica - alumina catalyst at 390 - 430 °C. All three possible methylamines are produced. The reaction proceeds to thermodynamic equilibrium, whose position is governed by the temperature and the nitrogen-carbon ratio ... The crude reaction mixture consists essentially of excess ammonia; mono-, di-, and trimethylamines; reaction water; and unconverted methanol. Purification is generally effected in a train of four to five distillation columns.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V21 694 (2003)

10.3 Impurities

Ammonia, no more than 0.2% by wt of solution; formaldehyde, no more than 0.3% by wt of solution
Flick, E.W. (ed.). Industrial Solvents Handbook 4 th ed. Noyes Data Corporation., Park Ridge, NJ., 1991., p. 710

10.4 Formulations / Preparations

Bull Run Fly Attractant (Bull Run Scientific, VBT): Active ingredient: sucrose 42.1%; indole 0.2%; yeast 5.5%; egg solids 18.0%; and trimethylamine 2.8%.
National Pesticide Information Retrieval System's Database on Trimethylamine (75-50-3). Available from, as of February 22, 2018: https://npirspublic.ceris.purdue.edu/ppis/
Starbar Fly Attractant (Central Garden & Pet Company): Active ingredient: indole 0.2%; cis-9-tricosene 1.0%; egg solids 20.5%; and trimethylamine 0.6%.
National Pesticide Information Retrieval System's Database on Trimethylamine (75-50-3). Available from, as of February 22, 2018: https://npirspublic.ceris.purdue.edu/ppis/
Grades: Anhydrous 99% minimum; aqueous soln 25, 30, 40%.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1378
Sold as 25% water solution or as liquified gas.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1668
For more Formulations/Preparations (Complete) data for Trimethylamine (6 total), please visit the HSDB record page.

10.5 Consumption Patterns

89% AS A CHEM INT FOR CHOLINE CHLORIDE (ANIMAL FEED SUPPLEMENT); AND 11% IN OTHER APPLICATIONS (1972)
SRI
CHEMICAL PROFILE: Methylamines. Tri: choline chloride, 80%; others, including biocides and slimicides, 20%.
Kavaler AR; Chemical Marketing Reporter 233 (5): 50 (1988)
CHEMICAL PROFILE: Methylamines. Demand: 1987: 190 million lb; 1988: 195 million lb; 1992 /projected/: 205 million lb (Foreign trade is small). /Methylamines/
Kavaler AR; Chemical Marketing Reporter 233 (5): 50 (1988)
CHEMICAL PROFILE: Methylamines: Trimethylamine: Demand: 74 million pounds.
Anon. (2006) ICIS Chemical Businesss America, June 19, 2006

10.6 U.S. Production

Aggregated Product Volume

2019: 10,000,000 - <50,000,000 lb

2018: 50,000,000 - <100,000,000 lb

2017: 50,000,000 - <100,000,000 lb

2016: 50,000,000 - <100,000,000 lb

(1972) 1.3X10+10 GRAMS
SRI
(1974) 1.30X10+10 GRAMS
SRI
(1981) 34,557X10+3 lb
United States International Trade Commission. Synthetic Organic Chemicals-- United States Production and Sales, 1981. USITC Publications 1291 Washington, DC: United States International Trade Commission, 1981., p. 241
(1984) 1.39X10+10 g
USITC. SYN ORG CHEM-U.S. PROD/SALES 1984 p.254
For more U.S. Production (Complete) data for Trimethylamine (9 total), please visit the HSDB record page.

10.7 U.S. Imports

(1972) 3.69X10+8 GRAMS
SRI

10.8 U.S. Exports

(1972) 2.4X10+9 GRAMS
SRI

10.9 General Manufacturing Information

Industry Processing Sectors
  • Agriculture, Forestry, Fishing and Hunting
  • All Other Basic Organic Chemical Manufacturing
  • Oil and Gas Drilling, Extraction, and Support activities
EPA TSCA Commercial Activity Status
Methanamine, N,N-dimethyl-: ACTIVE
MOLASSED SUGAR-BEET PULP, BECAUSE OF ITS HIGH CONTENT OF BETAINES, CAUSES MILK TO BE TAINTED FROM FORMATION OF TRIMETHYLAMINE.
Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 201

11 Identification

11.1 Analytic Laboratory Methods

Method: OSHA PV2060; Procedure: gas chromatography using a flame ionization detector; Analyte: trimethylamine; Matrix: air; Detection Limit: 0.08 ppm.
U.S. Department of Labor/Occupational Safety and Health Administration's Index of Sampling and Analytical Methods. Trimethylamine (75-50-3). Available from, as of February 21, 2018: https://www.osha.gov/dts/sltc/methods/toc.html
Two-dimensional (2D) polyacrylic acid (PAA) nano-nets that comprise interlinked ultrathin nanowires with diameters of 10-30 nm are successfully prepared by a facile electro-netting process. Nano-nets feature a clear geometric characteristic with ideal and weighted Steiner networks due to the rapid phase separation process and its obeyed minimal energy principle. The versatile nano-nets create enhanced interconnectivity and additional surface area and facilitate the diffusion of analytes into the membranes, which significantly boost the gas diffusion coefficient and sensing properties. As one example, PAA membranes containing fibers and nano-nets used as sensing materials are deposited by electrospinning/electro-netting on an electrode of a quartz crystal microbalance (QCM) for trimethylamine (TMA) detection, which exhibits a quick response (~180 s), low detection limit (1 ppm) and ideal selectivity at room temperature.
Wang X et al; Nanoscale 3 (3): 911-5 (2011)
Trimethylamine (TMA) is a key measurement indicator for meat spoilage. In order to develop simple, cheap, and sensitive sensors for TMA detection, a nanoporous colorimetric sensor array (NCSA) was developed. A sol-gel method has been used to obtain TiO2 nanoporous film as substrate material to improve the sensitivity and stability of the CSA. The sensor enabled the visual detection of TMA gas from the permissible exposure limits (PEL) 10 ppm to 60 ppb concentrations with significant response. Principal component analysis (PCA) was used to characterize the functional relationship between the color difference data and TMA concentrations. Furthermore, the NCSA was used to predict the presence of TMA in Yao-meat. A partial least square (PLS) prediction model was obtained with the correlation coefficients of 0.896 and 0.837 in calibration and prediction sets, respectively. This research suggested that the NCSA offers a useful technology for quality evaluation of TMA in meat.
Xiao-wei H et al; Food Chem 197 (Pt A): 930-6 (2016)
A novel gas sensor based on composite films of poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonate) (PEDOT/PSS) and single-walled carbon nanotubes (SWCNTs) was fabricated for the detection of fishy trimethylamine (TMA) vapor. The SWCNTs were functionalized by O2 plasma treatment to improve their solubility in the polymeric matrix, and alternative current dielectrophoresis was utilized for the first time to assemble the PEDOT/PSS-SWCNTs composite film to enhance the response to TMA molecules. The high resolution transmission electron microscopy (HR-TEM) images showed that the SWCNTs maintained their bulk structure after O2 plasma functionalization. The scanning electron microscopy (SEM) images of the composite film showed that the oxidized SWCNTs were orderly arranged and uniformly dispersed into the polymer by dielectrophoresis. Compositional analyses of SWCNTs by X-ray photoelectron spectroscopy (XPS) suggested that O2 plasma functionalization could remove amorphous carbon from the nanotube surface and introduce more hydrophilic oxygen-containing groups, leading to the improvement of SWCNTs solubility in the polymeric matrix. Gas sensitivities of the composite films largely relied on the treatment conditions. Compared to the raw or acid-treated SWCNTs-doped composite films, the film doped with SWCNTs modified by O2 plasma at 30 W for 3 min exhibited the most sensitive and stable response characteristics to ppb-level TMA gas.
Guo X et al; Analyst 138 (18): 5265-73 (2013)
For more Analytic Laboratory Methods (Complete) data for Trimethylamine (17 total), please visit the HSDB record page.

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 8
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Pictogram(s)
Flammable
Compressed Gas
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H220 (22.5%): Extremely flammable gas [Danger Flammable gases]

H224 (78.8%): Extremely flammable liquid and vapor [Danger Flammable liquids]

H280 (19.7%): Contains gas under pressure; may explode if heated [Warning Gases under pressure]

H302 (77.7%): Harmful if swallowed [Warning Acute toxicity, oral]

H314 (77.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H315 (23.7%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (35.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H332 (> 99.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (36.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P203, P210, P222, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P362+P364, P363, P370+P378, P377, P381, P403, P403+P233, P403+P235, P405, P410+P403, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2224 reports by companies from 39 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

12.1.2 Hazard Classes and Categories

Flam. Gas 1 (22.5%)

Flam. Liq. 1 (78.8%)

Press. Gas (Comp.) (19.7%)

Acute Tox. 4 (77.7%)

Skin Corr. 1B (77.7%)

Skin Irrit. 2 (23.7%)

Eye Dam. 1 (35.4%)

Acute Tox. 4 (> 99.9%)

STOT SE 3 (36.3%)

Flammable gas - category 1

Gases under pressure

Acute toxicity - category 4

Specific target organ toxicity (single exposure) - category 3

Eye damage - category 1

Skin irritation - category 2

12.1.3 NFPA Hazard Classification

1 of 2
View All
NFPA 704 Diamond
3-4-0
NFPA Health Rating
3 - Materials that, under emergency conditions, can cause serious or permanent injury.
NFPA Fire Rating
4 - Materials that rapidly or completely vaporize at atmospheric pressure and normal ambient temperature or that are readily dispersed in air and burn readily.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

12.1.4 Health Hazards

VAPOR: POISONOUS IF INHALED. Irritating to eyes, nose, and throat. LIQUID: Will burn skin and eyes. Harmful if swallowed. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

May cause toxic effects if inhaled or ingested. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

· May cause toxic effects if inhaled or ingested.

· Contact with substance may cause severe burns to skin and eyes.

· Fire will produce irritating, corrosive and/or toxic gases.

· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.

· Runoff from fire control or dilution water may cause environmental contamination.

ERG 2024, Guide 118 (Trimethylamine, anhydrous)

· May cause toxic effects if inhaled.

· Vapors are extremely irritating.

· Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite.

· Fire will produce irritating, corrosive and/or toxic gases.

· Runoff from fire control or dilution water may cause environmental contamination.

12.1.5 Fire Hazards

FLAMMABLE. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)

ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

· Flammable/combustible material.

· May be ignited by heat, sparks or flames.

· Vapors may form explosive mixtures with air.

· Vapors may travel to source of ignition and flash back.

· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).

· Vapor explosion hazard indoors, outdoors or in sewers.

· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.

· Runoff to sewer may create fire or explosion hazard.

· Containers may explode when heated.

· Many liquids will float on water.

ERG 2024, Guide 118 (Trimethylamine, anhydrous)

· EXTREMELY FLAMMABLE.

· May be ignited by heat, sparks or flames.

· May form explosive mixtures with air.

· Vapors from liquefied gas are initially heavier than air and spread along ground.

· Vapors may travel to source of ignition and flash back.

· Some of these materials may react violently with water.

· Cylinders exposed to fire may vent and release flammable gas through pressure relief devices.

· Containers may explode when heated.

· Ruptured cylinders may rocket.

Extremely flammable. Gives off irritating or toxic fumes (or gases) in a fire. Gas/air mixtures are explosive.
Extremely flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

12.1.6 Hazards Summary

Has a highly offensive odor at < 1 ppm; TLV Basis is irritation (skin, eyes, and upper respiratory tract); [ACGIH] Liquid causes first degree burns on short exposure. [CHRIS ] Corrosive to skin; [Quick CPC] Possible frostbite from contact with liquid; [NIOSH] May cause permanent eye injury; Transient visual effects (blue haze or halo vision) occur at low concentrations; [CHEMINFO] May cause respiratory tract irritation and pulmonary edema; [ICSC]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
Quick CPC - Forsberg K, Mansdorf SZ. Quick Selection Guide to Chemical Protective Clothing, 5th Ed. Hoboken, NJ: Wiley-Interscience, 2007.

12.1.7 Fire Potential

Flammable gas.
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 49-152
A very dangerous fire hazard when exposed to heat or flame.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
Trimethylamine is a flammable gas or liquid.
Pohanish, R.P. (ed). Sittig's Handbook of Toxic and Hazardous Chemical Carcinogens 6th Edition Volume 1: A-K,Volume 2: L-Z. William Andrew, Waltham, MA 2012, p. 2646

12.1.8 Skin, Eye, and Respiratory Irritations

Potential symptoms of overexposure to trimethylamine are irritation of eyes, skin, nose, throat, respiratory system ... .
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799

12.2 Safety and Hazard Properties

12.2.1 Acute Exposure Guideline Levels (AEGLs)

12.2.1.1 AEGLs Table
AEGLs
AEGL 1: Notable discomfort, irritation, or certain asymptomatic non-sensory effects. However, the effects are not disabling and are transient and reversible upon cessation of exposure (Unit: ppm)
10 min
8.0
30 min
8.0
60 min
8.0
4 hr
8.0
8 hr
8.0
AEGLs
AEGL 2: Irreversible or other serious, long-lasting adverse health effects or an impaired ability to escape (Unit: ppm)
10 min
240
30 min
150
60 min
120
4 hr
67
8 hr
51
AEGLs
AEGL 3: Life-threatening health effects or death (Unit: ppm)
10 min
750
30 min
490
60 min
380
4 hr
220
8 hr
170
12.2.1.2 AEGLs Notes

Level of Distinct Odor Awareness = 0.00051 ppm

AEGLs Status: Interim

12.2.2 Flammable Limits

Lower flammable limit: 2.0% by volume; Upper flammable limit: 11.6% by volume
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-111
Flammability
Flammable Gas

12.2.3 Lower Explosive Limit (LEL)

2 % (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
2 % (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
2.0%

12.2.4 Upper Explosive Limit (UEL)

11.6 % (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
11.6 % (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
11.6%

12.2.5 Critical Temperature & Pressure

Critical temperature: 161 °C; Critical pressure: 41 atm
Flick, E.W. (ed.). Industrial Solvents Handbook 4 th ed. Noyes Data Corporation., Park Ridge, NJ., 1991., p. 710

12.2.6 Physical Dangers

The gas is heavier than air and may travel along the ground; distant ignition possible.
The vapour is heavier than air and may travel along the ground; distant ignition possible.

12.2.7 Explosive Limits and Potential

Moderately explosive in the form of vapor when exposed to heat or flame.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
LEL: 2%, UEL: 11.6%
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
Explosive limits , vol% in air: 2.0-11.6
Explosive limits , vol% in air: 2-16.6

12.2.8 NIOSH Recommendations

Recommended Exposure Limit: 10 Hour Time-Weighted Average: 10 ppm (24 mg/cu m).
NIOSH. NIOSH Pocket Guide to Chemical Hazards. Department of Health & Human Services, Centers for Disease Control & Prevention. National Institute for Occupational Safety & Health. DHHS (NIOSH) Publication No. 2010-168 (2010). Available from: https://www.cdc.gov/niosh/npg
Recommended Exposure Limit: 15 Minute Short-Term Exposure Limit: 15 ppm (36 mg/cu m).
NIOSH. NIOSH Pocket Guide to Chemical Hazards. Department of Health & Human Services, Centers for Disease Control & Prevention. National Institute for Occupational Safety & Health. DHHS (NIOSH) Publication No. 2010-168 (2010). Available from: https://www.cdc.gov/niosh/npg

12.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Skin First Aid
ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Refer for medical attention .
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
Ingestion First Aid
Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

12.3.1 First Aid

INHALATION: remove victim to fresh air and call a doctor; give artificial respiration and oxygen if needed.

EYES: flush with water for at least 15 minutes; consult an eye doctor.

SKIN: flush with water, wash with soap and water. (USCG, 1999)

U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: CAUTION: Exposure of skin to compressed gases may result in freezing of the skin. Treatment for frostbite may be necessary. Remove the victim from the source of contamination. IMMEDIATELY wash affected areas gently with COLD water (and soap, if necessary) while removing and isolating all contaminated clothing. Dry carefully with clean, soft towels. Call a hospital or poison control center IMMEDIATELY even if no symptoms (such as inflammation or irritation) develop. Be prepared to transport the victim to a hospital for treatment after washing the affected area if advised to do so by a physician.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: This compound is a gas, therefore inhalation is the first route of exposure. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

General First Aid:

· Call 911 or emergency medical service.

· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.

· Move victim to fresh air if it can be done safely.

· Administer oxygen if breathing is difficult.

· If victim is not breathing:

-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingestedor inhaled the substance.

-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).

-- If no pulse detected or no respiratory medical device available, provide continuouscompressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.

· Remove and isolate contaminated clothing and shoes.

· For minor skin contact, avoid spreading material on unaffected skin.

· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.

· For severe burns, immediate medical attention is required.

· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.

· Keep victim calm and warm.

· Keep victim under observation.

· For further assistance, contact your local Poison Control Center.

· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.

Specific First Aid:

· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

· In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin.

In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section.

ERG 2024, Guide 118 (Trimethylamine, anhydrous)

General First Aid:

· Call 911 or emergency medical service.

· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.

· Move victim to fresh air if it can be done safely.

· Administer oxygen if breathing is difficult.

· If victim is not breathing:

-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingestedor inhaled the substance.

-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).

-- If no pulse detected or no respiratory medical device available, provide continuouscompressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.

· Remove and isolate contaminated clothing and shoes.

· For minor skin contact, avoid spreading material on unaffected skin.

· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.

· For severe burns, immediate medical attention is required.

· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.

· Keep victim calm and warm.

· Keep victim under observation.

· For further assistance, contact your local Poison Control Center.

· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.

Specific First Aid:

· In case of contact with liquefied gas, only medical personnel should attempt thawing frosted parts.

· In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin.

In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section.

(See general first aid procedures)

Eye: Irrigate immediately (liquid/solution)/Frostbite

Skin: Water flush immediately (liquid/solution)/Frostbite

Breathing: Respiratory support

Swallow: Medical attention immediately (solution)

12.4 Fire Fighting

Excerpt from ERG Guide 118 [Gases - Flammable - Corrosive]:

DO NOT EXTINGUISH A LEAKING GAS FIRE UNLESS LEAK CAN BE STOPPED.

SMALL FIRE: Dry chemical or CO2.

LARGE FIRE: Water spray, fog or regular foam. If it can be done safely, move undamaged containers away from the area around the fire. Damaged cylinders should be handled only by specialists.

FIRE INVOLVING TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Do not direct water at source of leak or safety devices; icing may occur. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

Some of these materials may react violently with water.

SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam.

LARGE FIRE: Water spray, fog or alcohol-resistant foam. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal. Do not get water inside containers.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Shut off supply; if not possible and no risk to surroundings, let the fire burn itself out. In other cases extinguish with powder, carbon dioxide. In case of fire: keep cylinder cool by spraying with water. Combat fire from a sheltered position.
Use water in large amounts, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

12.4.1 Fire Fighting Procedures

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Use water spray to cool unopened containers.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Trimethylamine, anhydrous/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 914
For more Fire Fighting Procedures (Complete) data for Trimethylamine (8 total), please visit the HSDB record page.

12.4.2 Firefighting Hazards

Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions.
Pohanish, R.P. (ed). Sittig's Handbook of Toxic and Hazardous Chemical Carcinogens 6th Edition Volume 1: A-K,Volume 2: L-Z. William Andrew, Waltham, MA 2012, p. 2646
Vapors are heavier than air and may travel to a source of ignition and flash back. Aqueous solutions are flammable unless diluted extensively.
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 49-152
Cylinders and tanks may rocket under fire conditions.
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 49-152

12.5 Accidental Release Measures

Public Safety: ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep unauthorized personnel away.

· Stay upwind, uphill and/or upstream.

· Ventilate closed spaces before entering, but only if properly trained and equipped.

Spill or Leak: ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· All equipment used when handling the product must be grounded.

· Do not touch or walk through spilled material.

· Stop leak if you can do it without risk.

· Prevent entry into waterways, sewers, basements or confined areas.

· A vapor-suppressing foam may be used to reduce vapors.

· Absorb with earth, sand or other non-combustible material.

· For hydrazine, absorb with DRY sand or inert absorbent (vermiculite or absorbent pads).

· Use clean, non-sparking tools to collect absorbed material.

Large Spill

· Dike far ahead of liquid spill for later disposal.

· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

Public Safety: ERG 2024, Guide 118 (Trimethylamine, anhydrous)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep unauthorized personnel away.

· Stay upwind, uphill and/or upstream.

· Many gases are heavier than air and will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).

· Ventilate closed spaces before entering, but only if properly trained and equipped.

Spill or Leak: ERG 2024, Guide 118 (Trimethylamine, anhydrous)

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· All equipment used when handling the product must be grounded.

· Do not touch or walk through spilled material.

· Stop leak if you can do it without risk.

· If possible, turn leaking containers so that gas escapes rather than liquid.

· Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material.

· Do not direct water at spill or source of leak.

· Isolate area until gas has dispersed.

12.5.1 Isolation and Evacuation

Excerpt from ERG Guide 118 [Gases - Flammable - Corrosive]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 100 meters (330 feet) in all directions.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, consider initial evacuation for 1600 meters (1 mile) in all directions. (ERG, 2024)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 50 meters (150 feet) in all directions.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Evacuation: ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

Immediate precautionary measure

· Isolate spill or leak area for at least 50 meters (150 feet) in all directions.

Spill

· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.

· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.

Fire

· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Evacuation: ERG 2024, Guide 118 (Trimethylamine, anhydrous)

Immediate precautionary measure

· Isolate spill or leak area for at least 100 meters (330 feet) in all directions.

Spill

· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.

· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.

Fire

· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, consider initial evacuation for 1600 meters (1 mile) in all directions.

12.5.2 Spillage Disposal

Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Remove all ignition sources. NEVER direct water jet on liquid. Remove vapour with fine water spray.
Evacuate danger area! Remove all ignition sources. Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Remove vapour with fine water spray.

12.5.3 Cleanup Methods

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Clean up promptly by sweeping or vacuum.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Neutralize with sodium bisulfate (NaHSO4). /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ /Trimethylamine, anhydrous/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 914
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply "universal" gelling agent to immobilize spill. Neutralize with sodium bisulfate (NaHSO4). /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ /Trimethylamine, aqueous solutions/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 915
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use surface active agent (e.g. detergent, soaps, alcohols), if approved by EPA. Inject "universal" gelling agent to solidify encircled spill and increase effectiveness of booms. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Add sodium bisulfate (NaHSO4). Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Trimethylamine, anhydrous/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 914
For more Cleanup Methods (Complete) data for Trimethylamine (12 total), please visit the HSDB record page.

12.5.4 Disposal Methods

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).

12.5.5 Preventive Measures

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
For more Preventive Measures (Complete) data for Trimethylamine (14 total), please visit the HSDB record page.

12.6 Handling and Storage

12.6.1 Nonfire Spill Response

Excerpt from ERG Guide 118 [Gases - Flammable - Corrosive]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. If possible, turn leaking containers so that gas escapes rather than liquid. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Do not direct water at spill or source of leak. Isolate area until gas has dispersed. (ERG, 2024)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb with earth, sand or other non-combustible material. For hydrazine, absorb with DRY sand or inert absorbent (vermiculite or absorbent pads). Use clean, non-sparking tools to collect absorbed material.

LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024)

12.6.2 Safe Storage

Fireproof. Cool.
Fireproof. Well closed. Separated from strong acids, oxidants, aluminium, copper, copper alloys, zinc, zinc alloys and mercury.

12.6.3 Storage Conditions

Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature 2-8 °C Contents under pressure. Moisture sensitive. Refrigerate before opening. Storage class (TRGS 510): Gases.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Store separately from all other flammable materials. Prior to working with this chemical you should be trained on its proper handling and storage. Before entering confined space where this chemical may be present, check to make sure that an explosive concentration does not exist. Trimethylamine must be stored to avoid contact with strong oxidizers (such as chlorine, bromine, and fluorine) and mercury since violent reactions occur. Sources of ignition, such as smoking and open flames, are prohibited where trimethylamine is used, handled, or stored in a manner that could create a potential fire or explosion hazard. Use only nonsparking tools and equipment, especially when opening and closing containers of trimethylamine. Wherever trimethylamine is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings. Procedures for the handling, use, and storage of cylinders should be in compliance with OSHA 1910.101 and 1910.169, as with the recommendations of the Compressed Gas Association.
Pohanish, R.P. (ed). Sittig's Handbook of Toxic and Hazardous Chemical Carcinogens 6th Edition Volume 1: A-K,Volume 2: L-Z. William Andrew, Waltham, MA 2012, p. 2646
Avoid oxidizing materials, acids, and sources of halogens. Store in cool, dry, well-ventilated location.
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 49-152

12.7 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.

· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

Maximum Allowable Concentration (MAK)
2.0 [ppm]

12.7.2 Permissible Exposure Limit (PEL)

12.7.3 Immediately Dangerous to Life or Health (IDLH)

N.D.

See: IDLH INDEX

12.7.4 Threshold Limit Values (TLV)

5.0 [ppm]
TLV-STEL
15.0 [ppm]
8 hr Time Weighted Avg (TWA): 5 ppm; 15 min Short Term Exposure Limit (STEL): 15 ppm.
American Conference of Governmental Industrial Hygienists TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH 2017, p. 60
5 ppm as TWA; 15 ppm as STEL.
TLV-TWA (Time Weighted Average)
5 ppm [2012]
TLV-STEL (Short Term Exposure Limit)
15 ppm [2012]

12.7.5 Occupational Exposure Limits (OEL)

EU-OEL
4,9 mg/m
MAK (Maximale Arbeitsplatz Konzentration)
4.9 mg/m

12.7.6 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 132 (Trimethylamine, aqueous solution)

· Some of these materials may react violently with water.

Small Fire

· Dry chemical, CO2, water spray or alcohol-resistant foam.

Large Fire

· Water spray, fog or alcohol-resistant foam.

· If it can be done safely, move undamaged containers away from the area around the fire.

· Dike runoff from fire control for later disposal.

· Do not get water inside containers.

Fire Involving Tanks, Rail Tank Cars or Highway Tanks

· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.

· Cool containers with flooding quantities of water until well after fire is out.

· Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

· ALWAYS stay away from tanks in direct contact with flames.

· For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

Emergency Response: ERG 2024, Guide 118 (Trimethylamine, anhydrous)

· DO NOT EXTINGUISH A LEAKING GAS FIRE UNLESS LEAK CAN BE STOPPED.

Small Fire

· Dry chemical or CO2.

Large Fire

· Water spray, fog or regular foam.

· If it can be done safely, move undamaged containers away from the area around the fire.

· Damaged cylinders should be handled only by specialists.

Fire Involving Tanks

· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.

· Cool containers with flooding quantities of water until well after fire is out.

· Do not direct water at source of leak or safety devices; icing may occur.

· Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

· ALWAYS stay away from tanks in direct contact with flames.

ERPG-1: 0.1 ppm - one hour exposure limit: 1 = mild transient health effects or objectionable odor [AIHA]

ERPG-2: 100 ppm - one hour exposure limit: 2 = impaired ability to take protective action [AIHA]

ERPG-3: 500 ppm - one hour exposure limit: 3 = life threatening health effects [AIHA]

Emergency Response Planning Guidlines (ERPGs) for trimethylamine:
ERPG / LEL
ERPG-1: The maximum airborne concentration below which it is believed nearly all individuals could be exposed for up to 1 hour without experiencing more than mild, transient adverse health effects or without perceiving a clearly defined objectionable odor.
Airborne Concentration
0.1 ppm
Notations
Odor should be detectable near ERPG-1
ERPG / LEL
ERPG-2: The maximum airborne concentration below which it is believed nearly all individuals could be exposed for up to 1 hour without experiencing or developing irreversible or other serious health effects or symptoms that could impair an individual's ability to take protective action.
Airborne Concentration
100 ppm
ERPG / LEL
ERPG-3: The maximum airborne concentration below which it is believed nearly all individuals could be exposed for up to 1 hour without experiencing or developing life-threatening health effects.
Airborne Concentration
500 ppm
ERPG / LEL
LEL (Lower Explosive Limit): The minimum concentration in air of a flammable gas or vapor at which ignition can occur.
Airborne Concentration
None
2017 Emergency Response Planning Guidelines (ERPG) & Workplace Environmental Exposure Level (WEEL). American Industrial Hygiene Association, Falls Church, VA 2017, p. 30

12.7.7 Other Standards Regulations and Guidelines

Workplace Environmental Exposure Level (WEEL): 8-hr Time-weighted Average (TWA) 1 ppm. Last Revised: 2005.
Toxicology Excellence for Risk Assessment; Occupational Alliance for Risk Science - Workplace Environmental Exposure Levels. Trimethylamine (75-50-3). Available from, as of February 20, 2018: https://www.tera.org/OARS/WEEL.html

12.7.8 Inhalation Risk

A harmful concentration of this gas in the air will be reached very quickly on loss of containment.
A harmful contamination of the air will be reached very quickly on evaporation of this substance at 20 °C.

12.7.9 Effects of Short Term Exposure

The substance is severely irritating to the eyes and respiratory tract. Rapid evaporation of the liquid may cause frostbite. Inhalation may cause lung oedema. The effects may be delayed. Medical observation is indicated.
The substance is corrosive to the eyes and skin. The vapour is severely irritating to the respiratory tract. Corrosive on ingestion.

12.7.10 Personal Protective Equipment (PPE)

Wear goggles and self-contained breathing apparatus. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE. Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Skin protection: Handle with gloves.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Body Protection: Complete suit protecting against chemicals. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type AXBEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
For more Personal Protective Equipment (PPE) (Complete) data for Trimethylamine (12 total), please visit the HSDB record page.

(See personal protection and sanitation codes)

Skin: Prevent skin contact (liquid/solution)/Frostbite

Eyes: Prevent eye contact (liquid/solution)/Frostbite

Wash skin: When contaminated (solution)

Remove: When wet (flammable)

Change: No recommendation

Provide: Eyewash (liquid/solution), Quick drench (liquid/solution), Frostbite wash

12.7.11 Respirator Recommendations

12.7.12 Preventions

Fire Prevention
NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Use non-sparking handtools.
Exposure Prevention
STRICT HYGIENE!
Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Cold-insulating gloves. Protective clothing.
Eye Prevention
Wear safety goggles or eye protection in combination with breathing protection.
Ingestion Prevention
Do not eat, drink, or smoke during work.
Exposure Prevention
AVOID ALL CONTACT!
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear face shield or eye protection in combination with breathing protection.

12.8 Stability and Reactivity

12.8.1 Air and Water Reactions

Highly flammable and easily ignited. Water soluble.
Highly flammable. Soluble in water.

12.8.2 Reactive Group

Amines, Phosphines, and Pyridines

Amines, Phosphines, and Pyridines

Water and Aqueous Solutions

12.8.3 Reactivity Alerts

Highly Flammable
12.8.3.1 CSL Reaction Information
CSL No
Reactants/Reagents
Ethylene oxide + Trimethylamine
Warning Message
Exothermic reaction resulted in an explosion and fire
GHS Category
Explosive,Flammable
Reaction Scale
Not Available
Reference Source
User Reported
Modified Date
04/22/2022
Create Date
04/21/2022

12.8.4 Reactivity Profile

TRIMETHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Contamination of an ethylene oxide tank with trimethylamine caused an explosion [BCISC Quart. Safety Summ., 1966, 37, 44].
TRIMETHYLAMINE, AQUEOUS SOLUTION neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Contamination of an ethylene oxide tank with trimethylamine caused an explosion [BCISC Quart. Safety Summ., 1966, 37, 44].

12.8.5 Hazardous Reactivities and Incompatibilities

Incompatible materials: Strong oxidizing agents, brass, magnesium, zinc, copper, mercury/mercury oxides, tin/tin oxides.
Sigma-Aldrich; Safety Data Sheet for Trimethylamine. Product Number: 243205, Version 4.7 (Revision Date 05/24/2016).
Self-reactive.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
Can react with oxidizing materials.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
Potentially explosive reaction with bromine + heat, ethylene oxide, triethynylaluminum.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3577
For more Hazardous Reactivities and Incompatibilities (Complete) data for Trimethylamine (9 total), please visit the HSDB record page.

12.9 Transport Information

12.9.1 DOT Emergency Guidelines

/GUIDE 118 GASES - FLAMMABLE - CORROSIVE/ Fire or Explosion: EXTREMELY FLAMMABLE. May be ignited by heat, sparks or flames. May form explosive mixtures with air. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Some of these materials may react violently with water. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket. /Trimethylamine, anhydrous/
U.S. Department of Transportation. 2016 Emergency Response Guidebook. Washington, D.C. 2016
/GUIDE 118 GASES - FLAMMABLE - CORROSIVE/ Health: May cause toxic effects if inhaled. Vapors are extremely irritating. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution. /Trimethylamine, anhydrous/
U.S. Department of Transportation. 2016 Emergency Response Guidebook. Washington, D.C. 2016
/GUIDE 118 GASES - FLAMMABLE - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Many gases are heavier than air and will spread along ground and collect in low or confined areas (sewers, basements, tanks). Ventilate closed spaces before entering. /Trimethylamine, anhydrous/
U.S. Department of Transportation. 2016 Emergency Response Guidebook. Washington, D.C. 2016
/GUIDE 118 GASES - FLAMMABLE - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Trimethylamine, anhydrous/
U.S. Department of Transportation. 2016 Emergency Response Guidebook. Washington, D.C. 2016
For more DOT Emergency Guidelines (Complete) data for Trimethylamine (16 total), please visit the HSDB record page.

12.9.2 DOT ID and Guide

12.9.3 Shipping Name / Number DOT/UN/NA/IMO

UN 1083; Trimethylamine, anhydrous
UN 1297; Trimethylamine, aqueous solutions with not more than 50% trimethylamine by mass
IMO 2.1; Trimethylamine, anhydrous
IMO 3.0; Trimethylamine, aqueous solution not more than 50% trimethylamine by mass

12.9.4 Standard Transportation Number

49 055 40; Trimethylamine, anhydrous
49 078 80; Trimethylamine, aqueous solution

12.9.5 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2 (USDOT); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 20, 2018: https://www.ecfr.gov
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Trimethylamine, anhydrous and trimethylamine, aqueous solution 50% or less trimethylamine, by mass are included on the dangerous goods list. /Trimethylamine, anhydrous; Trimethylamine, aqueous solution 50% or less trimethylamine, by mass/
International Air Transport Association. Dangerous Goods Regulations. 59th Edition. Montreal, Quebec Canada. 2018., p. 354
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. Trimethylamine, anhydrous; and trimethylamine, aqueous solution not more than 50% trimethylamine, by mass are included on the dangerous goods list. /Trimethylamine, anhydrous; Trimethylamine, aqueous solution not more than 50% trimethylamine, by mass/
International Maritime Organization. IMDG Code. International Maritime Dangerous Goods Code Volume 2 2016, p. 46, 57

12.9.6 DOT Label

Flammable Gas
Flammable Liquid Corrosive

12.9.7 Packaging and Labelling

Do not transport with food and feedstuffs.

12.9.8 EC Classification

Symbol: F+, Xn; R: 12-20-37/38-41; S: (2)-16-26-39
Symbol: F+, C; R: 12-20/22-34; S: (1/2)-3-16-26-29-36/37/39-45; Note: B

12.9.9 UN Classification

UN Hazard Class: 2.1
UN Hazard Class: 3; UN Subsidiary Risks: 8; UN Pack Group: I

12.10 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Methanamine, N,N-dimethyl-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Trimethylamine, anhydrous: HSNO Approval: HSR001014 Approved with controls

12.10.1 DHS Chemicals of Interest (COI)

Chemicals of Interest(COI)
Trimethylamine
Release: Minimum Concentration (%)
1
Release: Screening Threshold Quantities (in pounds)
10000
Security Issue: Release - Flammables
Flammable chemical that can be released at a facility.

12.10.2 Atmospheric Standards

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Trimethylamine is produced, as an intermediate or a final product, by process units covered under this subpart.
40 CFR 60.489 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 16, 2018: https://www.ecfr.gov

12.10.3 Clean Water Act Requirements

Trimethylamine is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
40 CFR 116.4 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 16, 2018: https://www.ecfr.gov

12.10.4 CERCLA Reportable Quantities

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
40 CFR 302.4 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 16, 2018: https://www.ecfr.gov

12.11 Other Safety Information

12.11.1 Toxic Combustion Products

Poisonous gases are produced in fire, including oxides of nitrogen.
Pohanish, R.P. (ed). Sittig's Handbook of Toxic and Hazardous Chemical Carcinogens 6th Edition Volume 1: A-K,Volume 2: L-Z. William Andrew, Waltham, MA 2012, p. 2646

12.11.2 Other Hazardous Reactions

Gas and aqueous solutions are corrosive.
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 49-152

13 Toxicity

13.1 Toxicological Information

13.1.1 Toxicity Summary

IDENTIFICATION AND USE: Trimethylamine (TMA) is a colorless gas. It is used in the manufacture of quaternary ammonium compounds, as an insect attractant, as a warning agent for natural gas, and as a corrosion inhibitor. It is also a synthetic flavor ingredient. HUMAN STUDIES: Potential symptoms of overexposure to TMA are irritation of the eyes, skin, nose, throat, and respiratory system, as well as cough, dyspnea, delayed pulmonary edema, blurred vision, corneal necrosis, and skin burns. Direct contact with liquid may cause frostbite. Trimethylaminuria or 'fish odor syndrome' described in human patients is due to excessive excretion into body fluids and breath of TMA derived from the enterobacterial metabolism of dietary precursors. Comparison of the effects of administration of antibiotics (metronidazole, amoxicillin, neomycin) on gut bacterial production of TMA from choline showed they all reduced TMA production to a limited extent, with neomycin being most effective. ANIMAL STUDIES: Tests of single drops of aqueous solution applied to animal eyes have shown that 1% solution causes severe irritation, 5% causes hemorrhagic conjunctivitis, and 16.5% causes a severe reaction with conjunctival hemorrhages, corneal edema, and opacities, followed by some clearing but much vascularization. TMA is an emetic in dogs at an oral dose of 1000 mg/kg. At the same oral dose, TMA induced emesis and produced anorexia, paralysis, and death in pigs within 48 hours. In a repeated inhalation exposure study, groups of rats were exposed 6 hr/day, 5 days/week for 2 weeks at 0, 75, 250, or 750 ppm TMA vapor. After 10 exposures, histopathologic examination revealed concentration-dependent degenerative changes in the nasal olfactory and respiratory mucosa at all exposure levels. A similar degeneration of the tracheal mucosa was observed at 250 and 750 ppm. In mice, intraperitoneal injections (daily from day 1 to 17 of gestation) of TMA at 2.5 and 5 mmol/kg/day significantly decreased fetal body weight but not the placental weight or maternal body weight gain, however, 5 of 11 mice treated with 5 mmol/kg TMA died. TMA was tested in as many as 5 Salmonella typhimurium strains (TA 1535, TA 1537, TA 97, TA 98, and TA 100) in the presence and absence of metabolic activation. TMA was negative in these tests at doses of 0.010, 0.033, 0.10, 0.33 and 1.0 mg/plate. The highest ineffective dose tested in any S. typhimurium strain was 1.000 mg/plate. ECOTOXICITY STUDIES: TMA caused inhibition to nitrifiers. Inhibition tests were conducted by using the oxygen utilization rate test with an enhanced nitrifier culture.
Uremic toxins such as trimethylamine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
A7868: Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. PMID:25041433
A7869: Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. PMID:22419041

13.1.2 NIOSH Toxicity Data

13.1.3 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

13.1.4 Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

13.1.5 Exposure Routes

The substance can be absorbed into the body by inhalation.
The substance can be absorbed into the body by inhalation of its vapour and by ingestion.
inhalation, ingestion (solution), skin and/or eye contact
Endogenous, Ingestion, Dermal (contact)

13.1.6 Symptoms

Inhalation Exposure
Burning sensation. Cough. Headache. Sore throat. Laboured breathing. Shortness of breath. Symptoms may be delayed.
Skin Exposure
ON CONTACT WITH LIQUID: FROSTBITE.
Eye Exposure
Redness. Pain. Blurred vision.
Inhalation Exposure
Burning sensation. Cough. Headache. Sore throat. Laboured breathing. Shortness of breath.
Skin Exposure
Redness. Pain. Skin burns.
Eye Exposure
Redness. Pain. Blurred vision. Severe deep burns.
Ingestion Exposure
Abdominal pain. Burning sensation. Shock or collapse.
irritation eyes, skin, nose, throat, respiratory system; cough, dyspnea (breathing difficulty), delayed pulmonary edema; blurred vision, corneal necrosis; skin burns; liquid: frostbite
As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

13.1.7 Target Organs

Eyes, skin, respiratory system

13.1.8 Adverse Effects

Dermatotoxin - Skin burns.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

13.1.9 Acute Effects

13.1.10 Toxicity Data

LCLo (rat) = 3,500 ppm/4h

13.1.11 Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

13.1.12 Interactions

Quinine specifically blocks connexin 36 (Cx36), one of the proteins that form gap junction channels. Quinine suppressed ictal /SRP: seizure/ epileptiform activity in in vitro and in vivo studies without decreasing neuronal excitability. In this study, we considered the possible mechanism of anticonvulsant effects of quinine (1, 250, 500, 1000 and 2000 uM, i.c.v.) in the pentylenetetrazole (PTZ) model of seizure. Thus, we used trimethylamine (TMA) (0.05 uM, 5 uM, 50 uM), a gap junction channel opener, to examine whether it could reverse the effects of quinine in rats. Intracerebroventricular (i.c.v.) injection of quinine affected generalized tonic-clonic seizure (GTCS) induced by PTZ by increments in seizure onset and reducing seizure duration. Additionally, pretreatment with different doses of TMA (i.c.v.) attenuated the anticonvulsant effects of quinine on the latency and duration of GTCS. It can be concluded that quinine possesses anticonvulsant effects via modulation of gap junction channels, which could contribute to the control of GTCS.
Nassiri-Asl M et al; Prog Neuropsychopharmacol Biol Psychiatry 32 (6): 1496-500 (2008)

13.1.13 Antidote and Emergency Treatment

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 194
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 194-5
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 195
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. ... Medical observation is recommended for 24-48 hr after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a corticosteroid spray.
Pohanish, R.P. (ed). Sittig's Handbook of Toxic and Hazardous Chemical Carcinogens 6th Edition Volume 1: A-K,Volume 2: L-Z. William Andrew, Waltham, MA 2012, p. 2646

13.1.14 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Potential symptoms of overexposure to trimethylamine are irritation of eyes, skin, nose, throat, respiratory system; cough, dyspnea, delayed pulmonary edema; blurred vision, corneal necrosis; skin burns; direct contact with liquid may cause frostbite.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1799
/SIGNS AND SYMPTOMS/ TMA was corrosive to human skin and eyes. A concentrated aqueous solution applied to intact human skin caused severe burning and hyperemia. Petechial hemorrhages appear on the skin even when the solution was washed away with soap and water within minutes of application. The exposed skin remained tender for 1 to 2 hours and slight desquamation was observed 2 to 3 hours later.
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 3
/SIGNS AND SYMPTOMS/ Accidental human eye contact with TMA caused corneal epithelial sloughing; the initial damage was followed by prompt healing with no sign of either corneal or other ocular injury within 4 to 5 days. In this case, the amount and concentration of TMA involved were not known; however, the exposure was suspected to be minimal.
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 3
/CASE REPORTS/ In an accident a student placed a glass ampule of liquified trimethylamine in dry ice and was attempting to open it when it exploded. The student was wearing glasses, but a blast of vapor struck one eye. There were no mechanical injuries, but it was very soon observed that the epithelium had been lost from the cornea. The epithelium healed promptly. There was no edema of the corneal stroma, and the eye was entirely normal within 4 to 5 days.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 952
For more Human Toxicity Excerpts (Complete) data for Trimethylamine (7 total), please visit the HSDB record page.

13.1.15 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Trimethylamine oxidation in chickens in vivo was rapidly and severely depressed by feeding goitrogenic thionamides (oxazolidine-2-thionine, 5-vinyl derivative of oxazolidine-2-thionine, 1-methyl-2-mercaptoimidazole, and thiourea). The effect of the 5-vinyl derivative of oxazolidine-2-thionine was not diminished by injecting large doses of triiodothyronine, thyroxine, or TSH simultaneously, and recovery was complete within 48 hr. These compounds strongly inhibited trimethylamine oxidase in hepatic microsomes. Hence, their short-term effect on trimethylamine oxidation is probably due to inhibition of the oxidase rather than being related to their antithyroid activity.
Pearson AW et al; Comp Biochem Physiol 69C (2): 307-12 (1981)
/LABORATORY ANIMALS: Acute Exposure/ ... Female Wistar rats (8 weeks old) /were exposed/ to 3040-7455 ppm TMA for 4 hours at 21.8-29.4 °C in a series of five experiments using 44 groups of 10 rats. The test concentrations were not stated, but were a geometric progression series using a factor of 1.05-1.15. A control group was included. The chamber humidity, temperature, and CO2 content (<0.2 vol %) were controlled and TMA concentration was monitored by gas chromatography. Animals were observed during exposure and for 14 days post-exposure. During exposure, the rats were initially restless but within a half hour appeared apathetic, had splayed hind- or forelimbs, inspirational dyspnea, and occasional uncoordinated movements and convulsions. During the second half-hour of exposure, the rats had marked hyperhidrosis (excessive sweating) and increased apathy and intensity of central nervous system effects, which consisted of sudden convulsions or muscle tremors that interrupted the somnolent state of the animals. The rats also had prolific nasal secretions, lacrimation, hemorrhage from the corners of the eyes and nasal orifices, and cyanosis of the ears. The first deaths occurred after 2 hours of exposure, and most animals died during the 4th exposure hour, typically following convulsions; the last animal died on day 4. Post-exposure signs included severe apathy, swelling of nasal orifices, dried bloody excretions, anorexia, and general ill health. These signs disappeared rapidly in the surviving animals. The calculated LC50 values (method of Spearman and Karber and probit analysis) decreased as temperature increased, and were approximately 4350 ppm at 21.8 °C, 3910 ppm at 25.7 °C, 3840 ppm at 27.0 °C, and 3380 ppm at 29 °C. ... 82 of the rats /were histologicall examined/. The 82 rats consisted of 63 rats that died during or after exposure (mean survival time of 3.3 hours), and 19 rats that survived 28 days (until sacrifice). ... The animals were examined macroscopically and the lungs, liver, kidneys, heart, skeletal muscle, and brain were examined microscopically. In the premature decedents, macroscopic abnormalities included marked blood profusion of the liver, spleen, and kidneys, and lung lobular hyperemia. Microscopic lung changes consisted of lobular red areas, bronchial inflammation with desquamation of the bronchial epithelium, bronchopneumonia in a few cases, and perivascular and peribronchial edema. Liver lesions included perilobular fatty liver, liver cell degeneration, and hyperemia. Most animals had lower nephron necrosis and vascular hyperemia of the kidneys, heart muscle, and many had brain edema and hyperemia. The surviving rats had few pathological changes, including one case of bronchopneumonia and three of lower nephron necrosis.
National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances (NAC/AEGL Committee); Acute Exposure Guideline Levels (AEGLs) for Trimethylamine (Interim) (CAS 75-50-3) p.11 (2008). Available from, as of February 5, 2018: https://www.epa.gov/aegl/trimethyl-amine-results-aegl-program
/LABORATORY ANIMALS: Acute Exposure/ In an inhalation LC50 study, CD Sprague-Dawley rats (5/sex/dose; 49-82 days old) were exposed whole-body to anhydrous TMA for 6 minutes (18,600 ppm), 10 minutes (18,100 ppm), 20 minutes (11,200-18,200 ppm), or 60 minutes (6150-8170 ppm). ... Exposure concentrations were generated by diluting TMA gas with air, and were quantitated by IR spectroscopy. Animals were observed daily for 14 days, weighed on days 0, 7, and 14, and survivors sacrificed on day 14. All animals were necropsied. The rats had decreased body weight gain primarily during the 1st week, and all groups exhibited gasping, labored breathing, rales, increased salivation, and corneal opacity immediately after exposure. The respiratory changes persisted throughout the study in only the 20 and 60 minute exposure groups, whereas corneal opacity persisted in all groups. Necropsy revealed eye lesions (cloudy cornea) in a few animals with no dose-response, and dose-related increases in the incidence of lung congestion (red, discolored lungs), which generally correlated with lethality. Lethality occurred in all groups treated for >/= 10 minutes, was generally dose-related, and primarily occurred immediately after exposure. The LC50 values [and 95% confidence limits] were 12,000 ppm [10,800-13,100 ppm] for 20 minutes and 7910 ppm [7300-8560 ppm] for 60 minutes, as calculated by the method of C.I. Bliss (1938). Subsequent analysis of the mortality data using EPA BenchMark dose software (Version 1.3.2.) yielded 20-minute values of LC50= 11,870 ppm, BMC01= 7420 ppm, and BMCL05= 5720 ppm; and 60-minute values of LC50= 8010 ppm, BMC01= 6330 ppm, and BMCL05= 4100 ppm. The statistical confidence was greater for the 60-minute values (p = 0.50) than for the 20-minute values (p = 0.069).
National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances (NAC/AEGL Committee); Acute Exposure Guideline Levels (AEGLs) for Trimethylamine (Interim) (CAS 75-50-3) p.11-2 (2008). Available from, as of February 5, 2018: https://www.epa.gov/aegl/trimethyl-amine-results-aegl-program
/LABORATORY ANIMALS: Acute Exposure/ ... TMA acute toxicity /was studied/ in 7-8 week old male CD (SD)BR rats. The TMA atmosphere was generated by dilution of TMA gas with 15 L/min air, and TMA air concentration was measured every 30 minutes with a Miran 1A infrared spectrometer. Rats (6/group) were exposed to 2000 or 3500 ppm TMA for 4 hrs, observed and weighed daily for two weeks, and the survivors sacrificed. Neither gross nor microscopic pathology were evaluated. No animals died in the 2000 ppm group, whereas at 3500 ppm TMA 3/6 animals died during exposure. During the exposure, all rats were immobile and did not react to sound, and exhibited difficulty breathing, and nasal and oral discharge. After exposure, survivors had moderate to severe (unspecified) weight loss for days 1-2, and lung noise for days 1-9. At 3500 ppm, rats also had dry red nasal and ocular discharge at the beginning of the post-exposure period.
National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances (NAC/AEGL Committee); Acute Exposure Guideline Levels (AEGLs) for Trimethylamine (Interim) (CAS 75-50-3) p.12 (2008). Available from, as of February 5, 2018: https://www.epa.gov/aegl/trimethyl-amine-results-aegl-program
For more Non-Human Toxicity Excerpts (Complete) data for Trimethylamine (18 total), please visit the HSDB record page.

13.1.16 Non-Human Toxicity Values

LD50 Rat oral 500 mg/kg
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2
LD50 Mouse (male) iv 90 mg/kg
American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2
LC50 Mouse (male) inhalation 7850 ppm/2 hr
National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances (NAC/AEGL Committee); Acute Exposure Guideline Levels (AEGLs) for Trimethylamine (Interim) (CAS 75-50-3) p.13 (2008). Available from, as of February 5, 2018: https://www.epa.gov/aegl/trimethyl-amine-results-aegl-program

13.1.17 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for trimethylamine is available.[Available from, as of March 27, 2018: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]
EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of March 27, 2018: http://actor.epa.gov/dashboard/]

13.1.18 Populations at Special Risk

Persistent trimethylaminuria in children is caused by autosomal recessively inherited impairment of hepatic trimethylamine (TMA) oxidation due to deficiency of flavin monooxygenase 3 (FMO3) secondary to mutations in the FMO3 gene. ... Comparison of the effects of administration of antibiotics (metronidazole, amoxicillin, neomycin) on gut bacterial production of trimethylamine from choline showed they all reduced TMA production to a limited extent, with neomycin being most effective. /Hepatic trimethylamine/
Chalmers RA et al; J Inherit Metab Dis 29 (1): 162-72 (2006)
... Following oral absorption in humans, Trimethylamine (TMA) undergoes efficient N-oxidation to trimethylamine-N-oxide (TMNO), a reaction catalyzed by the flavin-containing monooxygenase (FMO) isoform 3 enzyme ... Trimethylaminuria is a condition that is characterized by a deficiency in FMO3 enzyme activity, resulting in the excretion of increased amounts of TMA in bodily fluids such as urine and sweat, and breath. A human FMO3 database has been established and currently twenty-eight variants of the FMO3 gene have been reported including twenty-four missense, three nonsense, and one gross deletion mutation ...
Bain MA et al; Curr Drug Metab 6(3):227-40 (2005)
Persistent trimethylaminuria in children is caused by autosomal recessively inherited impairment of hepatic trimethylamine (TMA) oxidation due to deficiency of flavin monooxygenase 3 (FMO3) secondary to mutations in the FMO3 gene. Trimethylaminuria or 'fish odor syndrome' is due to excessive excretion into body fluids and breath of TMA derived from the enterobacterial metabolism of dietary precursors. The disorder is present from birth but becomes apparent as foods containing high amounts of choline or of trimethylamine N-oxide (TMAO) from marine (sea or saltwater) fish are introduced into the diet. ... Trimethylaminuria (FMO3 deficiency) in children is rare. ... /The present study/ compared the dynamics and diagnostic efficacy of choline loading with marine fish meals in six children with trimethylaminuria. Loading with a marine fish meal provides a simple and acceptable method for confirmation of diagnosis of suspected trimethylaminuria in children, with the effects being cleared more quickly than with a choline load test. However, oral loading with choline bitartrate allows estimation of residual oxidative capacity in vivo and is a useful adjunct to molecular studies. Patients homozygous for the 'common' P153L mutation in the FMO3 gene showed virtual complete lack of residual TMA N-oxidative capacity, consistent with a nonfunctional or absent FMO3 enzyme, whereas a patient with the M82T mutation showed some residual oxidative capacity. A patient compound heterozygous for two novel mutations, G193E and R483T, showed considerable residual N-oxidative capacity. A further patient, heterozygous for two novel sequence variations in the FMO3 gene, consistently showed malodor and elevated urinary TMA/TMAO ratios under basal conditions but a negative response to both choline and marine fish meal loading. Comparison of the effects of administration of antibiotics (metronidazole, amoxicillin, neomycin) on gut bacterial production of trimethylamine from choline showed they all reduced TMA production to a limited extent, with neomycin being most effective. /Hepatic trimethylamine/
Chalmers RA et al; J Inherit Metab Dis 29 (1): 162-72 (2006)

13.2 Ecological Information

13.2.1 Ecotoxicity Values

EC50; Species: Anabaena subcylindrica (Blue-green algae) axenic, 1-3x10+7 cells/mL; Conditions: freshwater, static, 25 °C, pH 7.2; Concentration: 2.58x10-7 ug/cell for < or =3 hr; Effect: physiology, nitrogen fixation
Mosier AR; J Environ Qual 7 (2): 237-40 (1978) as cited in the ECOTOX database. Available from, as of January 30, 2018
EC50; Species: Anabaena subcylindrica (Blue-green algae) axenic, 1-3x10+7 cells/mL; Conditions: freshwater, static, 25 °C, pH 7.2; Concentration: 2.04x10-7 ug/cell for < or =3 hr; Effect: physiology, decreased photosynthesis
Mosier AR; J Environ Qual 7 (2): 237-40 (1978) as cited in the ECOTOX database. Available from, as of January 30, 2018
EC50; Species: Chlorella ellipsoidea (Green algae) axenic; Conditions: freshwater, static, 25 °C, pH 7.2; Concentration: 2.4x10-8 ug/cell for 90 min; Effect: physiology, decreased photosynthesis
Mosier AR; J Environ Qual 7 (2): 237-40 (1978) as cited in the ECOTOX database. Available from, as of January 30, 2018
LC50; Species: Oryzias latipes (Medaka) length 2 cm, weight 0.2 g; Conditions: freshwater, static, 25 °C; Concentration: 1000000 ug/L for 24 hr
Tonogai Y et al; J Toxicol Sci 7 (3): 193-203 (1982) as cited in the ECOTOX database. Available from, as of January 30, 2018
LC50; Species: Oryzias latipes (Medaka) length 2 cm, weight 0.2 g; Conditions: freshwater, static, 25 °C; Concentration: 1000000 ug/L for 48 hr /Conditions of bioassay not specified in source examined/
Tonogai Y et al; J Toxicol Sci 7 (3): 193-203 (1982) as cited in the ECOTOX database. Available from, as of January 30, 2018

13.2.2 Ecotoxicity Excerpts

/AQUATIC SPECIES/ This research compared the toxicity and inhibition caused by three aliphatic amines (n-propylamine, ethylmethylamine, and trimethylamine) and their chlorinated derivatives. The chemistry of chlorine interactions with these compounds was characterized by using membrane introduction mass spectrometry (MIMS). Acute toxicity assays were conducted by using a Microtox system with Phosphobacterium phosphoreum (also known as Vibrio fischeri) for the aliphatic amine compounds and their corresponding chlorinated derivatives, as identified by MIMS. Inhibition tests were conducted by using the oxygen utilization rate test with an enhanced nitrifier culture. The median effective concentration (EC50) values for chloropropylamine, chloroethylmethylamine, and chlorodimethylamine obtained by Microtox with a contact time of 15 min were 12.68, 19.72, and 15.92 uM, respectively. The EC50 values of these aliphatic chloramines from the Microtox test decreased by roughly one order of magnitude as a result of chlorination. Inhibition of nitrifiers also was observed in these amines. Trimethylamine and n-propylamine caused greater inhibition to nitrifiers than did ethylmethylamine under similar concentrations. Nitrifier inhibition from these amines increased after chlorination. The results of these tests indicated that aliphatic amines and their chlorinated derivatives could induce environmentally relevant toxicity responses in treatment settings and in receiving waters.
Gong WL et al; Environ Toxicol Chem 23 (2): 239-44 (2004)

13.2.3 Environmental Fate / Exposure Summary

Trimethylamine's production and use in organic synthesis, as a warning agent for natural gas, in the manufacture of disinfectants, as a flotation agent, as an insect attractant, in the production of quaternary ammonium compounds and plastics may result in its release to the environment through various waste streams. Trimethylamine is found in nature, and widely distributed in the environment as a result of its formation during the decay of organic matter in vegetation, fish, sewage, animals and animal waste. If released to air, a vapor pressure of 1610 mm Hg at 25 °C indicates trimethylamine will exist solely as a gas in the atmosphere. Gas-phase trimethylamine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl and nitrate radicals; the half-lives for these reactions in air are estimated to be 6 hours and 76 days, respectively. Trimethylamine does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, trimethylamine is expected to have very high mobility based upon an estimated Koc of 7. The pKa of trimethylamine is 9.8, indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the compound exists as an cation and cations do not volatilize. Trimethylamine may volatilize from dry soil surfaces based upon its vapor pressure. Utilizing the Japanese MITI test, 92% of the Theoretical BOD was reached in 2 weeks indicating that biodegradation is an important environmental fate process. Microbial production of dimethylamine from trimethylamine in soil was found to be greater under acidic conditions than at near neutral pH and greater under aerobic conditions than anaerobic conditions. If released into water, trimethylamine is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Trimethylamine incubated in a marine sediment slurry underwent about 35% removal in 12 hrs. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's pKa. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to trimethylamine may occur through inhalation and dermal contact with this compound at workplaces where trimethylamine is produced or used. Monitoring data indicate that the general population may be exposed to trimethylamine via inhalation of tobacco smoke and ingestion of food containing trimethylamine. (SRC)

13.2.4 Natural Pollution Sources

Trimethylamine forms as a result of microbial breakdown of both choline and betaine, common constituents of plants and animals, and from bacterial reduction of trimethylamine N-oxide, a common metabolite and excretory product of aquatic organisms(1-3). Trimethylamine also occurs in nature as a degradation product of nitrogenous plant and animal tissues(1,2,4,5).Trimethylamine has been reported in some plants(6).
(1) Oremland RS et al; Nature 296: 143-45 (1982)
(2) Hippe H et al; Proc Natl Acad Sci USA 76: 494-98 (1979)
(3) Graedel TE; Chemical Compounds in the Atmosphere. New York, NY: Academic Press (1978)
(4) Cavender FL; Aliphatic and Alicyclic Amines. Patty's Toxicology. 6th ed. (1999-2018). New York, NY: John Wiley & Sons, Inc. On-line Posting Date: 17 Aug 2012.
(5) O'Neil MJ, ed; The Merck Index. 15th ed. Cambridge, UK: The Royal Society of Chemistry. p. 1799 (2013)
(6) US Dept Agric; US Dept Agric, Agric Res Service. 1992-2016. Dr. Duke's Phytochemical and Ethnobotanical Databases. Trimethylamine. Available from, as of March 6, 2018: https://phytochem.nal.usda.gov/phytochem/search

13.2.5 Artificial Pollution Sources

Trimethylamine's production and use in organic synthesis, as a warning agent for natural gas, in the manufacture of disinfectants, as a flotation agent, as an insect attractant, for the production of quaternary ammonium compounds and plastics(1) may result in its release to the environment through various waste streams(SRC).
(1) Larranaga MD et al; Hawley's Condensed Chemical Dictionary 16th ed., Hoboken, NJ: John Wiley & Sons, Inc., p. 1378 (2016)

13.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a structure estimation method(2), indicates that trimethylamine is expected to have very high mobility in soil(SRC). The pKa of trimethylamine is 9.8(3), indicating that this compound will exist almost entirely in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Sorption coefficients for trimethylamine adsorption on montmorillonite, kaolinite and Flax Pond sediment were 15, 2 and 7 mL/g, respectively(5). The trimethylamine cation adsorbed strongest to the negatively-charged montmorillonite via electrostatic interactions(5). Volatilization of the cation from moist soil is not expected because cations do not volatilize(SRC). Trimethylamine is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1610 mm Hg at 25 °C(6). Microbial production of dimethylamine from trimethylamine in soil was found to be greater under acidic conditions than at near neutral pH and greater under aerobic conditions than anaerobic conditions(7). Degradation products formed under aerobic conditions include dimethylamine, formaldehyde, formate and carbon dioxide(8), while products formed under anaerobic conditions include dimethylamine, ammonia and methane(9).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of March 6, 2018: https://www2.epa.gov/tsca-screening-tools
(3) Perrin DD; Dissociation Constants of Organic Bases in Aqueous Solution. IUPAC Chem Data Ser: Suppl 1972. Buttersworth, London (1972)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Wang XC, Lee C; Mar Chem 44: 1-23 (1993)
(6) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng, New York, NY: Hemisphere Pub Corp, 5 Vol (1989)
(7) Tate RL, Alexander M; Appl Environ Microbiol 31: 399-403 (1976)
(8) Meiberg JBM, Harber W; J Gen Microbiol 106: 265-76 (1978)
(9) Hippe H et al; Proc Natl Acad Sci USA 76: 494-98 (1977)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a structure estimation method(2), indicates that trimethylamine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 9.8(3) indicates trimethylamine will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). Trimethylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.16(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Trimethylamine incubated in a marine sediment slurry underwent about 35% removal in 12 hrs, as measured by production of carbon dioxide and methane(7). Degradation products formed under aerobic conditions include dimethylamine, formaldehyde, formate and carbon dioxide(8), while products formed under anaerobic conditions include dimethylamine, ammonia and methane(9). Trimethylamine achieved 92% of its Theoretical BOD in 2 weeks using an activated sludge inoculum in the Japanese MITI test(10).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of March 6, 2018: https://www2.epa.gov/tsca-screening-tools
(3) Perrin DD; Dissociation Constants of Organic Bases in Aqueous Solution. IUPAC Chem Data Ser: Suppl 1972. Buttersworth, London (1972)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 9 (1995)
(7) King GM et al; Appl Environ Microbiol 45: 1848-53 (1983)
(8) Tate RL, Alexander M; Appl Environ Microbiol 31: 399-403 (1976)
(9) Meiberg JBM, Harber W; J Gen Microbiol 106: 265-76 (1978)
(10) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of March 6, 2018: https://www.safe.nite.go.jp/english/db.html
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethylamine, which has a vapor pressure of 1610 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase trimethylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl and nitrate radicals(SRC); the half-lives for these reactions in air are estimated to be 6 hours and 76 days(SRC), calculated from respective rate constants of 6.09X10-11(3) and 4.4X10-16(4) cu cm/molecule-sec at 25 °C(SRC). Trimethylamine does not contain chromophores that absorb at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng, New York, NY: Hemisphere Pub Corp, 5 Vol (1989)
(3) Atkinson R; J Phys Chem Ref Data. Monograph 1 (1989)
(4) Silva PJ et al; Environ Sci Technol 42: 4689-96 (2008)
(5) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12, 8-13 (1990)

13.2.7 Environmental Biodegradation

AEROBIC: Numerous strains of bacteria isolated from seawater, lake water, mud, garden soil, and activated sludge have been found capable of growth on trimethylamine(1-4). A mixed culture of microorganisms in a mineral salt medium degraded 24% of the initial trimethylamine added to dimethylamine after 36 hours of incubation(3). Trimethylamine reached 77.2% of its Theoretical BOD incubated with activated sludge for 13 days(5). Microbial production of dimethylamine from trimethylamine in soil was found to be greater under acidic conditions than at near neutral pH and greater under aerobic conditions than anaerobic conditions(6). Degradation products formed under aerobic conditions include dimethylamine, formaldehyde, formate and carbon dioxide(7). Trimethylamine, present at 100 mg/L, reached 92% of its Theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(8).
(1) Troyan OS et al; Samooch Bioindik Zagraz Vod Moscow, USSR pp. 196-99 (1977)
(2) Kimura T et al; Bull Fac Fish 4: 1-9 (1977)
(3) Ayanabe A, Alexander M; Appl Microbiol 25: 862-69 (1973)
(4) Colby J, Zatman LJ; Biochem J 132: 101-12 (1973)
(5) Chudoba J et al; Chem Prum 20: 2079-100 (1969)
(6) Tate RL, Alexander M; Appl Environ Microbiol 31: 399-403 (1976)
(7) Meiberg JBM, Harber W; J Gen Microbiol 106: 265-76 (1978)
(8) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of March 1, 2018: https://www.safe.nite.go.jp/english/db.html
ANAEROBIC: In hypersaline Algal mat (St. Croix, US Virgin Islands) sediment, patterns of substrate metabolism suggest that trimethylamine was degraded by methanogenic bacterial populations to produce methane gas(1). Trimethylamine incubated in a marine sediment (Lowes Cove, ME) slurry underwent about 35% removal, as measured by production of carbon dioxide and methane, in 12 hours(2). Biodegradation of trimethylamine accounted for 35.1 to 61.1% of total methane produced in these marine sediments(2). Biodegradation of trimethylamine accounted for 90% of total methane produced in anoxic salt marsh sediment amended with Spartina foliosa(3). Microbial production of dimethylamine from trimethylamine in soil was found to be greater under acidic conditions than at near neutral pH and greater under aerobic conditions than anaerobic conditions(4). Products formed under anaerobic conditions include dimethylamine, ammonium and methane(5). Trimethylamine was readily biodegraded when incubated at 35 °C for 50 days using sludge under anaerobic conditions(6).
(1) King GM; Appl Environ Microbiol 54: 130-6 (1988)
(2) King GM et al; Appl Environ Microbiol 45: 1848-53 (1983)
(3) Oremland RS et al; Nature 296: 143-5 (1982)
(4) Tate RL, Alexander M; Appl Environ Microbiol 31: 399-403 (1976)
(5) Hippe H et al; Proc Natl Acad Sci USA 76: 494-98 (1977)
(6) Hongwei Y et al; Ecotox Environ Saf 63: 299-305 (2006)

13.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of trimethylamine with photochemically-produced hydroxyl radicals has been reported as 6.09X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of trimethylamine with nitrate radicals is 4.4X10-16 cu cm/molecule-sec(2). This corresponds to an atmospheric half-life of approximately 76 days at an atmospheric concentration of 2.4X10+8 hydroxyl radicals per cu cm(3). Trimethylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Trimethylamine does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Atkinson R; J Phys Chem Ref Data. Monograph 1 (1989)
(2) Silva PJ et al; Environ Sci Technol 42: 4689-96 (2008)
(3) Atkinson R; J Phys Chem Ref Data. Monograph 2 (1994)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12, 8-13 (1990)

13.2.9 Environmental Bioconcentration

An estimated BCF of 3 was calculated in fish for trimethylamine(SRC), using a log Kow of 0.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 9 (1995)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of March 6, 2018: https://www2.epa.gov/tsca-screening-tools/
(3) Franke C et al; Chemosphere 29: 1501-14 (1994

13.2.10 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trimethylamine can be estimated to be 7(SRC). According to a classification scheme(2), this estimated Koc value suggests that trimethylamine is expected to have very high mobility in soil. The pKa of trimethylamine is 9.8(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Sorption coefficients for trimethylamine adsorption on montmorillonite, kaolinite and Flax Pond sediment (7% clay, 2.8% organic matter; Long Island, NY) were 15, 2 and 7 mL/g, respectively(5). The trimethylamine cation adsorbed strongest to the negatively-charged montmorillonite via electrostatic interactions(5).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of March 6, 2018: https://www2.epa.gov/tsca-screening-tools
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) Perrin DD; Dissociation Constants of Organic Bases in Aqueous Solution. IUPAC Chem Data Ser: Suppl 1972. Buttersworth, London (1972)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Wang XC, Lee C; Mar Chem 44: 1-23 (1993)

13.2.11 Volatilization from Water / Soil

A pKa of 9.8(1) indicates trimethylamine will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Trimethylamine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1610 mm Hg(2).
(1) Perrin DD; Dissociation Constants of Organic Bases in Aqueous Solution. IUPAC Chem Data Ser: Suppl 1972. Buttersworth, London (1972)
(2) Daubert TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. Design Inst Phys Prop Data, Amer Inst Chem Eng, New York, NY: Hemisphere Pub Corp, 5 Vol (1989)

13.2.12 Effluent Concentrations

The annual trimethylamine emissions from animal husbandry in developed countries is estimated to be 108 Gg nitrogen/yr(1).
(1) Schade GW, Crutzen PJ; J Atmos Chem 22: 319-46 (1995)

13.2.13 Sediment / Soil Concentrations

SOIL: Trimethylamine has been identified in uncultivated soil(1).
(1) Golovnya RV et al; USSR Acad Med Sci pp.327-35 (1982)

13.2.14 Atmospheric Concentrations

URBAN/SUBURBAN: Trimethylamine was detected in atmospheric particle samples obtained from 1998-1999 sampling in Osaka, Japan at trace levels (0.04 ng/cu m) to 0.18 ng/cu m(1). Urban atmospheric concentrations of trimethylamine have been reported as 4.0-80 parts/trillion(2). Trimethylamine was detected in 34 source and 16 ambient air samples collected in 2004 from the Thane Belapur Industrial Area, Mumbai, India(3).
(1) Suzuki Y et al; Environ Sci Technol 35: 2656-2564 (2001)
(2) Kieloaho AJ et al; Atmos Environ 80: 369-77 (2013)
(3) Srivastava A, Som D; Chemosphere 69: 458-68 (2007)
INDOOR: Using a direct sampling method, the mean trimethylamine concentration in a lot-parked car interior was 1.15 ug/cu m; samples were collected Aug 2006(1).
(1) Rampft M et al; Environ Sci Technol 42: 5217-22 (2008)
RURAL/REMOTE: Trimethylamine (in conjunction with propylamine) was detected in atmospheric samples collected May-Oct 2011 from a Scotch pine (Pinus sylvestris L.) forest located in Finland at 21 parts/trillion(1). Rural atmospheric concentrations of trimethylamine have been reported as 0.8-41 parts/trillion(1). Trimethylamine was detected in atmospheric particulates (0.52-1.9 um), concentrations were lowest at humidity of <30% and highest in the winter at humidity >90%(2).
(1) Kieloaho AJ et al; Atmos Environ 80: 369-77 (2013)
(2) Rehbein PJG et al; Environ Sci Technol 45: 4346-52 (2011)

13.2.15 Food Survey Values

Trimethylamine has been identified as a volatile component of boiled beef(1).
(1) Golovnya RV et al; Chem Sense Flavor 4: 97-105 (1974)

13.2.16 Plant Concentrations

Trimethylamine has been found to be a volatile constituent of marine algae(1).
(1) Steiner M, Hartman T; Planta 79: 113-21 (1968)
Trimethylamine has been reported, not quantified in plants(1).
Genus species
Acorus calamus
Family
Acoraceae
Common name(s)
Sweet Calamus
Part
plant
Genus species
Bryonia alba
Family
Cucurbitaceae
Common name(s)
White Bryony
Part
root
Genus species
Clematis vitalba
Family
Ranunculaceae
Common name(s)
Traveler's Joy
Part
plant
Genus species
Gymnema sylvestre
Family
Asclepiadaceae
Common name(s)
Miracle Fruit
Part
leaf
Genus species
Humulus lupulus
Family
Cannabaceae
Common name(s)
Hops
Part
fruit
Genus species
Medicago sativa
Family
Fabaceae
Common name(s)
Alfalfa
Part
plant
Genus species
Nicotiana tabacum
Family
Solanaceae
Common name(s)
Tobacco
Part
leaf
Genus species
Oryza sativa
Family
Poaceae
Common name(s)
Rice
Part
seed
Genus species
Sorbus aucubaria
Family
Rosaceae
Common name(s)
Rowan Berry
Part
flower
(1) US Dept Agric; US Dept Agric, Agric Res Service. 1992-2016. Dr. Duke's Phytochemical and Ethnobotanical Databases. Trimethylamine. Available from, as of March 6, 2018: https://phytochem.nal.usda.gov/phytochem/search

13.2.17 Fish / Seafood Concentrations

Trimethylamine was detected in fresh hake (Merluccius merluccius) caught off the Mediterranean coast near Barcelona at 0.17 mg/100 g, the concentration increased steadily to 21.57 mg/100 g after 16 days of storage on ice(1). Trimethylamine was detected at 0.33 mg/100 g in anchovy (Engraulis encrasicholus) caught off the Mediterranean coast near Barcelona(2). In anchovy (Engraulis encrasicholus) stored at 4 °C, trimethylamine concentrations rose from 3.68 to 287.66 mg/kg over 168 days(3). The concentration of trimethylamine in crab (Charybdis feriatus) meats was 869, 966 and 457 ug/kg in the leg, body and carapace, respectively(4). Trimethylamine was detected at average concentrations of 7430 and 3230 ng/g in boiled and steamed scallops (Chlamys farreri), respectively, respective concentrations in scallops (Patinopecten yessoensis) were 3190 and 2440 ng/g(5). Trimethylamine was identified, not quantified, in the volatile components of fish sauce(6). Trimethylamine was detected at 0.29 and 0.41 mg/100 g in anchovy (Engraluis encrasicholus) freshly packed and then marinated for 3 months, respectively(7). In blanched and fried prawn meat, average trimethylamine concentrations were reported as 580 and 450 ug/kg, respectively(8).
(1) Baixas-Nogueras S et al; J Agric Food Chem 49: 1681-6 (2001)
(2) Pons-Sanchez-Cascado S et al; J Agric Food Chem 53: 8586-92 (2005)
(3) Romero-Gonzalez R et al; J Agric Food Chem 60: 5324-9 (2012)
(4) Chung HY; J Agric Food Chem. 47: 2280-7 (1999)
(5) Chung HY et al; J Agric Food Chem 49: 192-202 (2001)
(6) Fukami K et al; J Agric Food Chem 50: 5412-5416 (2002)
(7) Pons-Sanchez-Cascado S et al; J Agric Food Chem 53: 8586-92 (2005)
(8) Mall V, Schieberle P; J Agric Food Chem 65: 2776-83 (2017)
Trimethylamine and dimethylamine contents of salted, hot-air dried and sun-dried samples of 2 commercial fishes, mackerel pike and seerfish, were analyzed and quantitatively compared at 3 different temperatures. The formation of both amines was more rapid at 10 and 15 °C than at 2 °C. Trimethylamine contents of hot-air dried mackerel pike and sun-dried seerfish were relatively higher than those in other samples, while those of salted samples were comparatively lower than those of others.
Park YH et al; Bull Korean Fish Soc 14 (1): 7-14 (1981)

13.2.18 Milk Concentrations

Trimethylamine was detected at 4 mM in commercial milk(1).
(1) Hu F et al; J Agric Food Chem 55: 4307-11 (2007)

13.2.19 Other Environmental Concentrations

Trimethylamine is a constituent of tobacco smoke(1). Trimethylamine was identified as a volatile component in cattle feed lots(2). In beef cattle feed yards, trimethylamine was reported as the primary odorant(3).
(1) Graedel TE; Chemical Compounds in the Atmosphere Academic Press New York, NY p.228 (1978)
(2) Mosier AR et al; Environ Sci Tech 7: 642-4 (1973)
(3) Wright DW et al; J Agric Food Chem 53: 8663-72 (2005)

13.2.20 Probable Routes of Human Exposure

According to the 2016 TSCA Inventory Update Reporting data, 6 reporting facilities estimate the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of trimethylamine in the United States may be as low as <10 workers up to the range of 500-999 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).
(1) US EPA; Chemical Data Reporting (CDR). Non-confidential 2016 Chemical Data Reporting information on chemical production and use in the United States. Available from, as of March 7, 2018: https://chemview.epa.gov/chemview
NIOSH (NOES Survey 1981-1983) has statistically estimated that 5261 workers (2870 of these are female) were potentially exposed to trimethylamine in the US(1). Occupational exposure to trimethylamine may occur through inhalation and dermal contact with this compound at workplaces where trimethylamine is produced or used. Monitoring data indicate that the general population may be exposed to trimethylamine via inhalation of tobacco smoke and ingestion of food containing trimethylamine(SRC).
(1) CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of March 6, 2018: https://www.cdc.gov/niosh/ipcs/default.html

13.2.21 Average Daily Intake

Annual consumption is 416.67 lb. Individual consumption is 0.0003631 mg/kg/day.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 5th ed.Boca Raton, FL 2005, p. 1824

14 Associated Disorders and Diseases

Disease
Pregnancy
References

PubMed: 2994907, 663967, 12698507, 17061063, 3252730, 12833386, 17704099, 16925883, 22420377, 18059417, 22494326, 23159745, 23313728, 23535240, 24704061

The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.

Disease
Perillyl alcohol administration for cancer treatment
References
Disease
Dimethylglycine Dehydrogenase Deficiency
References
PubMed: 10102904
Disease
Trimethylaminuria
References

PubMed: 9246418, 16601883, 7474897

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Disease
Irritable bowel syndrome
References
Disease
Kidney disease
References
Disease
Periodontal disease
References
PubMed: 20300169
Disease
Uremia
References

PubMed: 2026685, 8087979, 9607216, 17132244, 6520173, 21359215, 15353324, 11865086, 9573551, 10509899, 7482520, 19309105, 24023812, 22626821, 12675874

Merck Manual of Diagnosis and Therapy.

Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Geigy Scientific Tables, 8th Rev edition, pp. 80-82. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.

David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971

National Health and Nutrition Examination Survey (NHANES Survey) 2013

Disease
Pancreatic cancer
References
Disease
Diverticular disease
References
Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart
Disease
Early preeclampsia
References
PubMed: 22494326
Disease
Late-onset preeclampsia
References
PubMed: 23159745

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Wiley References

15.6 Nature Journal References

15.7 Chemical Co-Occurrences in Literature

15.8 Chemical-Gene Co-Occurrences in Literature

15.9 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

17.2 Chemical-Target Interactions

17.3 Pathways

18 Biological Test Results

18.1 BioAssay Results

19 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S29 | PHYTOTOXINS | Toxic Plant Phytotoxin (TPPT) Database | DOI:10.5281/zenodo.2652993

20 Classification

20.1 MeSH Tree

20.2 ChEBI Ontology

20.3 ChemIDplus

20.4 CAMEO Chemicals

20.5 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

20.6 ChEMBL Target Tree

20.7 UN GHS Classification

20.8 EPA CPDat Classification

20.9 NORMAN Suspect List Exchange Classification

20.10 EPA DSSTox Classification

20.11 EPA TSCA and CDR Classification

20.12 LOTUS Tree

20.13 EPA Substance Registry Services Tree

20.14 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
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    https://cameochemicals.noaa.gov/chemical/4713
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  19. Emergency Response Guidebook (ERG)
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  24. LOTUS - the natural products occurrence database
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  25. Toxin and Toxin Target Database (T3DB)
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  27. IUPAC Digitized pKa Dataset
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  30. Therapeutic Target Database (TTD)
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  34. KNApSAcK Species-Metabolite Database
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  37. EPA Chemical and Products Database (CPDat)
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  40. NITE-CMC
    Trimethylamine - FY2006 (New/original classication)
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    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
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  42. FDA Substances Added to Food
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
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  43. Flavor and Extract Manufacturers Association (FEMA)
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    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
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  45. MassBank Europe
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    The content of the MoNA database is licensed under CC BY 4.0.
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    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
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    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
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    Ethylene oxide + Trimethylamine
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  58. Protein Data Bank in Europe (PDBe)
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    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  60. Springer Nature
  61. SpringerMaterials
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    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
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  63. Wikidata
  64. Wikipedia
  65. Wiley
  66. PubChem
  67. Medical Subject Headings (MeSH)
    LICENSE
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