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Brucine

PubChem CID
442021
Structure
Brucine_small.png
Brucine_3D_Structure.png
Brucine__Crystal_Structure.png
Molecular Formula
Synonyms
  • BRUCINE
  • 357-57-3
  • 10,11-Dimethoxystrychnine
  • Brucinum
  • 2,3-Dimethoxystrychnine
Molecular Weight
394.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
Brucine appears as a white crystalline solid. Combustible but may require some effort to ignite. Toxic by inhalation (vapor, dust, etc.) and ingestion.
Brucine is a monoterpenoid indole alkaloid and an organic heteroheptacyclic compound.
Brucine has been reported in Strychnos ignatii, Strychnos wallichiana, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Brucine.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 4
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4aR,5aS,8aR,13aS,15aS,15bR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RRKTZKIUPZVBMF-IBTVXLQLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC1=C(C=C2C(=C1)[C@]34CCN5[C@H]3C[C@@H]6[C@@H]7[C@@H]4N2C(=O)C[C@@H]7OCC=C6C5)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C23H26N2O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)
C23H26N2O4

2.3 Other Identifiers

2.3.1 CAS

357-57-3
145428-94-0
5892-11-5
63428-84-2

2.3.3 Deprecated CAS

101324-32-7, 1087723-67-8, 1195340-33-0, 1195623-19-8, 193198-03-7, 462651-43-0, 54193-32-7, 70206-61-0
101324-32-7, 1195340-33-0, 1195623-19-8, 193198-03-7, 462651-43-0, 54193-32-7, 70206-61-0

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 ICSC Number

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 Pharos Ligand ID

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 10,11-dimethoxystrychnine
  • brucine
  • bruzin
  • dimethoxystrychnine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
394.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1
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
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
394.18925731 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
394.18925731 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
51.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
785
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
6
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

Brucine appears as a white crystalline solid. Combustible but may require some effort to ignite. Toxic by inhalation (vapor, dust, etc.) and ingestion.
Colorless or white odorless solid; Slightly soluble in water (3.2 g/L at 15 deg C); [HSDB] White powder; [MSDSonline]
COLOURLESS CRYSTALS OR WHITE CRYSTALLINE POWDER.

3.2.2 Color / Form

Needles from acetone + water
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 237
COLORLESS CRYSTAL OR WHITE, CRYSTALLINE POWDER
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1073
White, crystalline alkaloid
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 174
Colorless prisms (from ethanol/water)
American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices for 1993-1994. Cincinnati, OH: ACGIH, 1993., p. VA1 590

3.2.3 Odor

Odorless
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

3.2.4 Taste

Very bitter taste
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 174

3.2.5 Boiling Point

470 °C
Dixon D, Rissmann E; Physical-chemical properties and categorization of RCRA wastes according to votality. Springfield,VA: Versar, Inc. USEPA-450/3-85-007. (NTIS PB85-204527) p. 74 (1985)

3.2.6 Melting Point

352 °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.
178 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 174

3.2.7 Solubility

Crystals. Sol in water or alcohol. The solns are neutral or slightly acid. /Hydrochloride/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 238
Prisms, dec 230 °C. Sol in water or alcohol. /Nitrate dihydrate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 238
Slightly soluble in ethyl ether and benzene; very soluble in ethanol.
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-316
Slightly sol in water, ether, glycerin and ethyl acetate.
ITII. Toxic and Hazarous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute, 1982., p. 81
Soluble in alcohol, chloroform, and benzene; slightly soluble in ether, glycerol, and ethyl acetate.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 174
In water, 3.2X10+3 mg/l @ 15 °C
Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ Az, College of Pharmacy (1992)
Solubility in water: poor

3.2.8 Density

greater than 1 at 68 °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.

3.2.9 LogP

Log Kow= 0.98
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 180
0.98

3.2.10 Stability / Shelf Life

Stable /during transport/.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

3.2.11 Optical Rotation

Specific optical rotation: -127 deg/D (chloroform), -85 deg/D (abs alc); max absorption (ethanol): 263 NM (log e= 4.09)
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 237
SPECIFIC OPTICAL ROTATION: -149.5 DEG @ 20 °C/5461 D
Weast, R.C. (ed.) Handbook of Chemistry and Physics. 67th ed. Boca Raton, FL: CRC Press, Inc., 1986-87., p. C-161

3.2.12 Decomposition

When heated to decomposition it emits toxic fumes of nitroxides.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 534

3.2.13 Heat of Combustion

687.68 kg cal/g mole @ 25 °C (gas)
Weast, R.C. (ed.) Handbook of Chemistry and Physics. 67th ed. Boca Raton, FL: CRC Press, Inc., 1986-87., p. D-272

3.2.14 Dissociation Constants

pKa= 8.28 @ 25 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 8-56
Monoclinic prisms. Also forms a dihydrate. Very bitter taste. Bitterness threshold 1:220,000 ... Becomes anyhdr at 100 °C. One g dissolves in 0.8 ml methanol, 1.3 ml alcohol, 5 ml chloroform, 25 ml ethyl acetate, 36 ml glycerol, about 100 ml benzene, 187 ml ether, 1320 ml water, 750 ml boiling water. pH of satd water soln 9.5. pKa 6.04, pK2 11.7. /Tetrahydrate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 238

3.2.15 Collision Cross Section

179.91 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

189.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
192.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
190.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.2.16 Other Experimental Properties

AN ALKALOID OF NUX VOMICA; DIFFERS FROM STRYCHINE IN THAT IT CONTAINS 2 METHOXY GROUPS
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1073
Small, bitter crystals. One g dissolves in 75 ml cold water, about 10 ml boiling water, 105 ml alcohol, 170 ml chloroform. Soly in water is decreased by H2SO4. /Sulfate heptahydrate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 238

3.3 Chemical Classes

Biological Agents -> Plant Toxins

3.3.1 Cosmetics

Cosmetic ingredients (Brucine) -> CIR (Cosmetic Ingredient Review)

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
SADTLER REFERENCE NUMBER: 2252 (IR, PRISM), 8248 (IR, GRATING); 600 (UV); 683 (NMR)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian A-60
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
MCB Manufacturing Chemists, Norwood, Ohio
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
Source of Spectrum
Mass Spectrometry Committee of the Toxicology Section of the American Academy of Forensic Sciences
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. Portions provided by AAFS, Toxicology Section. All Rights Reserved.
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2 of 2
Source of Spectrum
Mass Spectrometry Committee of the Toxicology Section of the American Academy of Forensic Sciences
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. Portions provided by AAFS, Toxicology Section. All Rights Reserved.
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4.2.2 LC-MS

1 of 14
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Authors
Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil)
Instrument
maXis (Bruker Daltonics)
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm
Precursor Adduct
[M+H]+
Top 5 Peaks

395.1974 999

396.2005 220

397.2032 29

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License
CC BY
2 of 14
View All
Authors
Markus Kohlhoff, Natural Product Chemistry Lab (FIOCRUZ Minas, Brazil)
Instrument
maXis (Bruker Daltonics)
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm
Precursor Adduct
[M+H]+
Top 5 Peaks

395.197 999

396.2002 219

397.2029 32

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License
CC BY

4.2.3 Other MS

Other MS
MASS: 5060 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

4.3 UV Spectra

MAX ABSORPTION (ALCOHOL): 264 NM (LOG E= 4.01); 301 NM (LOG E= 3.94)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-216

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

4.4.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
399027
Lot Number
BCBG5589V
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
399027
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
399027
Lot Number
BCBG5589V
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Other Spectra

Intense mass spectral peaks: 355 m/z, 379 m/z, 394 m/z
Pfleger, K., H. Maurer and A. Weber. Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Parts I and II. Mass Spectra Indexes. Weinheim, Federal Republic of Germany. 1985., p. 643

6 Chemical Vendors

7 Drug and Medication Information

7.1 Therapeutic Uses

INDICATORS AND REAGENT
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
THE /BRUCINE/ SULFATE ... /HAS BEEN/ USED IN VET MEDICINE IN EQUAL PARTS WITH STRYCHNINE IN TONIC AND STIMULANT FORMULATIONS. /BRUCINE SULFATE/
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 53
/FORMERLY IN VET MEDICINE/ AS CNS STIMULANT.
Carmichael, W.W. (ed.). Environmental Science Research. Volume 20. The Water Environment-Algal Toxins and Health. New York/London: Plenum Press, 1981., p. 201

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Analgesics
Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)
Adjuvants, Immunologic
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)
Indicators and Reagents
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)

8.2 Metabolism / Metabolites

BRUCINE YIELDS BRUCINE-N-OXIDE IN BACILLUS; YIELDS 2-HYDROXY-3-METHOXYSTRYCHNINE & 3-HYDROXY-2-METHOXYSTRYCHNINE IN RABBITS.
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. B-26

9 Use and Manufacturing

9.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Brucine
Sources/Uses
Extracted from the seeds and bark of Strychnos aculeata; Used for denaturing alcohol and oils; Also used as an additive to lubricants, a rodent poison, a CNS stimulant, and a chemical reagent; [HSDB] A poison resembling strychnine that is much less potent; [Reference #1]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
DENATURANT FOR ETHANOL; REAGENT FOR SEPARATING RACEMIC MIXTURES.
SRI
Rodent poison.
SITTIG. HDBK TOX & HAZARD CHEM & CARCINOGENS 2ND ED 1985 p.152
THE MOST COMMON DENATURANT /FOR ETHANOL/ USED NOW ... IN COSMETIC PREPARATIONS ...
Arena, J.M. and Drew, R.H. (eds.) Poisoning-Toxicology, Symptoms, Treatments. 5th ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 273
MEDICATION (VET)
For more Uses (Complete) data for BRUCINE (7 total), please visit the HSDB record page.
Brucine is a plant toxin found in several species, most notably the Strychnine tree (Strychnos nux-vomica L.). Medically, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments. (L1227)
L1227: Wikipedia. Brucine. Last Updated 8 April 2009. http://en.wikipedia.org/wiki/Brucine

9.1.1 Use Classification

Hazard Classes and Categories ->

9.2 Methods of Manufacturing

EXTRACTED FROM THE SEEDS & BARK OF STRYCHNOS ACULEATA.
SRI
By extraction & subsequent crystallization from nux vomica or ignatia seeds.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 174
From Strychnos seeds (Strychnos nux-vomica L. and S. igantti Berg., Loganiaceae).
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 237
Prepn from strychnine, q.v.: E. Tedeschi et al., Tetrahedron 24, 4573 (1968); P. Rosenmund et al., Ber. 101, 2754 (1968).
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 237

9.3 Formulations / Preparations

Forms brucine sulfate, hydrochloride, & nitrate (mp 230 °C).
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 174
THE MOST COMMON DENATURANT /FOR ETHANOL/ USED NOW ... IN COSMETIC PREPARATIONS, IS SD-40 WHICH HAS THE FOLLOWING FORMULATIONS: 3 OZ OF BRUCINE (ALKALOID) OR BRUCINE SULFATE
Arena, J.M. and Drew, R.H. (eds.) Poisoning-Toxicology, Symptoms, Treatments. 5th ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 273
Alkaloid, NF grade; dihydrate, white powder grade; sulfate, NF grade
CHEMCYCLOPEDIA p. 265 (1986)
Available as the free base or as the sulfate salt.
Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 144

9.4 U.S. Imports

(1972) 2.12X10+7 GRAMS (BRUCINE & CMPDS)
SRI
(1975) 1.20X10+7 GRAMS (BRUCINE & CMPDS)
SRI
(1984) 2.84X10+8 g
BUREAU OF THE CENSUS. US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p.1-365

9.5 General Manufacturing Information

EPA TSCA Commercial Activity Status
Strychnidin-10-one, 2,3-dimethoxy-: ACTIVE

9.6 Sampling Procedures

Measurements to determine employee exposure are best taken so that the average eight hr exposure is based on a single eight hr sample or two four hr samples. Several short time interval samples (up to 30 min) may also be used to determine the average exposure level. Air samples should be taken in the employee's breathing zone (air that would most nearly represent that inhaled by the employee). /Strychnine/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 2

10 Identification

10.1 Analytic Laboratory Methods

TLC: WALDI, D, SCHNACKERZ, K & F MUNTER, J CHROMATOGR 6, 61 (1961); DICKES, GJ, APPLICATIONS OF TLC IN PUBLIC ANALYST'S LAB, J ASSOC PUBLIC ANALYSTS 4, 45 (1966). GLC: BROCHMANN-HANSSEN, E &A BAERHEIM SVENDSEN, J PHARM SCI 51, 1096 (1962); LLOYD, HA ET AL, SEPARATION OF ALKALOIDS BY GC, J AMER CHEM SOC 82, 3791 (1960).
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 19
A RAPID AND HIGHLY SELECTIVE METHOD FOR THE MICRODETERMINATION OF BRUCINE IN STRYCHNINE NITRATE BY RING OVEN TECHNIQUE WAS PRESENTED. NITRIC ACID WAS USED AS A DEVELOPING SOLN AND COLOR AGENT. THE DETECTION LIMIT WAS 0.2 UG.
CHIBA A; BULL CHEM SOC JPN 49 (8): 2323-4 (1976)
A cold extraction method followed by spectrophotometric detection was proposed for strychnine and brucine. The method is suitable for the analysis of dosage forms, powders, tinctures and dry experiments containing the alkaloids. A detailed description of the glass apparatus used for extraction was given. The sample is placed in the glass apparatus, washed sand, 28% NH3 and CHCl3 are added in the same order and the glass apparatus is shaken for 30 min and the absorbances are measured at 305 nm and 206 nm. The extraction method does not cause degradation of the alkaloids. The precision of the method is 2.5%.
Gaudy D, Puech A; Ann Pharm Fr 44 (1): 49-54 (1986)
Strychnine and brucine are extracted from Nux vomica extraction, diluted with water and NH4OH by using CHCl3 and are then back-extracted with 0.1 N H2SO4. The first derivative spectra are measured at 312 nm for brucine. The limits of detection were 3 ug/ml, and the mean recover was 100.4 for brucine.
Korany MA, Seif El-Din AA; J Assoc Off Anal Chem 67 (1): 138-41 (1984)
AOAC Method 930.40. Alkaloids and related amines in drugs. Microchemical tests.
Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC: Association of Analytical Chemists, 1990, p. 534

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 7
View All
Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H300+H330 (32.9%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P264, P270, P271, P273, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, 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 85 reports by companies from 3 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.

11.1.2 Hazard Classes and Categories

Acute Tox. 2 (100%)

Acute Tox. 2 (100%)

Aquatic Chronic 3 (100%)

Acute Tox. 2 (90.5%)

Acute Tox. 2 (100%)

Aquatic Chronic 3 (100%)

11.1.3 Health Hazards

Chemical is toxic if inhaled, swallowed, or absorbed through skin. Inhalation produces intense bitter taste. Ingestion causes nausea, vomiting, restlessness, excitement, twitching, and (rarely) convulsions. Contact with dust irritates eyes. (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.
ERG 2024, Guide 151 (Brucine)

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

· Avoid any skin contact.

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

· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

11.1.4 Fire Hazards

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires. (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.
ERG 2024, Guide 151 (Brucine)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

· Containers may explode when heated.

· Runoff may pollute waterways.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

11.1.5 Hazards Summary

An eye, nose and throat irritant; [HSDB] Oral LD50 (mouse) = 150 mg/kg; [RTECS] May cause convulsions and respiratory paralysis; [ICSC] An irritant; Effects in high-dose animal studies include convulsions; [MSDSonline]

11.1.6 Fire Potential

It is combustible though it may require some effort to ignite.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 165

11.1.7 Skin, Eye, and Respiratory Irritations

Irritating to eyes, nose, and throat.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

11.1.8 EPA Hazardous Waste Number

P018; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.

11.2 First Aid Measures

Inhalation First Aid
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap. 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.
Ingestion First Aid
Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention . Avoid unnecessary stimulation of the victim.

11.2.1 First Aid

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: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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: DO NOT INDUCE VOMITING. Strychnine is an exceptionally toxic poison but inducing vomiting may cause a seizure. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (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 151 (Brucine)

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.

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

11.3 Fire Fighting

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

SMALL FIRE: Dry chemical, CO2 or water spray.

LARGE FIRE: Water spray, fog or regular 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. Avoid aiming straight or solid streams directly onto the product.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. 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)

Use water spray, powder, foam, carbon dioxide.

11.3.1 Fire Fighting Procedures

Wear goggles and self-contained breathing apparatus /while fighting fires/. Extinguish with water, dry chemical, foam, or carbon dioxide.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, carbon dioxide.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 165

11.4 Accidental Release Measures

Public Safety: ERG 2024, Guide 151 (Brucine)

· 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.

Spill or Leak: ERG 2024, Guide 151 (Brucine)

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

· Stop leak if you can do it without risk.

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

· Cover with plastic sheet to prevent spreading.

· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.

· DO NOT GET WATER INSIDE CONTAINERS.

· For solids, prevent dust cloud and avoid inhalation of dust.

11.4.1 Isolation and Evacuation

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

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 151 (Brucine)

Immediate precautionary measure

· Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

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.

11.4.2 Spillage Disposal

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

11.4.3 Cleanup Methods

1. Ventilate area of spill. 2. Collect spilled material in the most convenient and safe manner and deposit in sealed containers for reclamation, or for disposal in a secured sanitary landfill. Liquid containing strychnine should be absorbed in vermiculite, dry sand, earth, or a similar material. /Strychnine/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 3
Pour into sodium bicarbonate or a mixture of sand-soda ash (9:1). After mixing, transfer into a paper carton filled with packing paper. Burn in an open furnace, or more efficiently in the furnace with afterburner and scrubber.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 82
Environmental considerations - Land spill. Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /Strychnine/
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 1007
Environmental considerations - Water spill; Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concn, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Strychnine/
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 1007
Spread over with 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper. Burn in an open furnace with the utmost care or in the furnace with afterburner and scrubber.
ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute, 1988., p. 494

11.4.4 Disposal Methods

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P018, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
40 CFR 240-280, 300-306, 702-799 (7/1/96)
(a) Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the solution into the furnace with afterburner and scrubber. (b) Pour into sodium bicarbonate or a mixture of sand-soda ash (9:1). After mixing, transfer into a paper carton filled with packing paper. Burn in an open furnace, or more efficiently in the furnace with afterburner and scrubber.
ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute, 1988., p. 82
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. /From table/
USEPA; Engineering Handbook for Hazardous Waste Incineration p.3-8 (1981) EPA 68-03-3025

11.4.5 Preventive Measures

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 165
Personnel protection: Avoid breathing vapors or dusts. Keep upwind. Wear positive pressure self-contained breathing apparatus. Avoid bodily contact with the material. Wear appropriate chemical protective clothing. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 165
If the use of respirators is necessary, the only respirators permitted are those that have been approved by the Mine Safety and Health Administration (formerly Mining Enforcement and Safety Administration) or by the National Institute for Occupational Safety and Health. /Strychnine/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 2
Skin that becomes contaminated with liquid strychnine should be immediately washed. /Strychnine/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 2
For more Preventive Measures (Complete) data for BRUCINE (11 total), please visit the HSDB record page.

11.5 Handling and Storage

11.5.1 Nonfire Spill Response

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. For solids, prevent dust cloud and avoid inhalation of dust. (ERG, 2024)

11.5.2 Safe Storage

Separated from strong oxidants and food and feedstuffs. Dry. Well closed.

11.5.3 Storage Conditions

Storage temperature: Ambient
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

11.6 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 151 (Brucine)

· 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.

11.6.1 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 151 (Brucine)

Small Fire

· Dry chemical, CO2 or water spray.

Large Fire

· Water spray, fog or regular 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.

· Avoid aiming straight or solid streams directly onto the product.

Fire Involving Tanks, Rail Tank Cars or Highway Tanks

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

· Do not get water inside containers.

· 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.

11.6.2 Inhalation Risk

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.

11.6.3 Effects of Short Term Exposure

May cause mechanical irritation. The substance may cause effects on the nervous system and eyes. This may result in convulsions and respiratory paralysis. Exposure could cause death.

11.6.4 Personal Protective Equipment (PPE)

Dust mask; goggles or face shield; rubber gloves (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.
/NIOSH approved respirator/; goggles or face shield.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
Wear butyl rubber gloves, full protective clothing, self-contained respirator and protective shoes.
ITII. Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute, 1988., p. 81
The following types of respirators should be selected under the prescribed concentrations: 0.75 mg/cu m: 1) Any dust and mist respirator, except single-use respirators. 1.5 mg/cu m: 1) Any dust and mist respirator, except single-use and quarter-mask respirators, 2) Any supplied-air respirator, 3) Any self-contained breathing apparatus. 3 mg/cu m: 1) Any powered air-purifying respirator with a dust and mist filter, 2) Any supplied-air respirator operated in a continuous flow mode, 3) Any air-purifying full facepiece respirator with a high-efficiency particulate filter, 4) Any supplied-air respirator with a full facepiece. 5) Any self-contained breathing apparatus with a full facepiece. Emergency or planned entry in unknown concentration or IDLH conditions: 1) Any self-contained breathing apparatus with a full facepiece and operated in a pressure-demand or other positive pressure mode, 2) Any supplied-air respirator with a full face piece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode. Escape: 1) Any air-purifying full facepiece respirator with a high-efficiency particulate filter, 2) Any appropriate escape-type self-contained breathing apparatus. /Strychnine/
NIOSH. Pocket Guide to Chemical Hazards. 5th Printing/Revision. DHHS (NIOSH) Publ. No. 85-114. Washington, D.C.: U.S. Dept. of Health and Human Services, NIOSH/Supt. of Documents, GPO, Sept. 1985., p. 210

11.6.5 Preventions

Fire Prevention
NO open flames.
Exposure Prevention
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Inhalation Prevention
Use ventilation (not if powder), local exhaust or breathing protection.
Skin Prevention
Protective gloves.
Eye Prevention
Wear safety goggles.
Ingestion Prevention
Do not eat, drink, or smoke during work. Wash hands before eating.

11.7 Stability and Reactivity

11.7.1 Air and Water Reactions

Slightly soluble in water.

11.7.2 Reactive Group

Amides and Imides

Amines, Phosphines, and Pyridines

Ethers

11.8 Transport Information

11.8.1 DOT Emergency Guidelines

/GUIDE 152: SUBSTANCES - TOXIC (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 152: SUBSTANCES - TOXIC (Combustible)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 152: SUBSTANCES - TOXIC (Combustible)/ 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 in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 152: SUBSTANCES - TOXIC (Combustible)/ 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.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
For more DOT Emergency Guidelines (Complete) data for BRUCINE (8 total), please visit the HSDB record page.

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

UN 1570; Brucine
IMO 6.1; Brucine
NA 2811; Brucine

11.8.3 Standard Transportation Number

49 214 11; Brucine, solid (dimethoxy strychnine)

11.8.4 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 (7/1/96)
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.
IATA. Dangerous Goods Regulations. 38th ed. Montreal, Canada and Geneva, Switzerland: International Air Transport Association, Dangerous Goods Board, January, 1997., p. 111
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.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.6083 (1988)

11.8.5 DOT Label

Poison

11.8.6 Packaging and Labelling

Do not transport with food and feedstuffs.

11.8.7 EC Classification

Symbol: T+; R: 26/28-52/53; S: (1/2)-13-45-61

11.8.8 UN Classification

UN Hazard Class: 6.1; UN Pack Group: I

11.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Strychnidin-10-one, 2,3-dimethoxy-
New Zealand EPA Inventory of Chemical Status
Brucine tetrahydrate: HSNO Approval: HSR006243 Approved with controls
New Zealand EPA Inventory of Chemical Status
Strychnidin-10-one, 2,3-dimethoxy-, dihydrate: Does not have an individual approval but may be used under an appropriate group standard

11.9.1 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; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
40 CFR 302.4 (7/1/98)

11.9.2 TSCA Requirements

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Brucine is included on this list.
40 CFR 716.120 (7/1/98)

11.9.3 RCRA Requirements

P018; As stipulated in 40 CFR 261.33, when brucine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).
40 CFR 261.33 (7/1/98)

11.10 Other Safety Information

Chemical Assessment
IMAP assessments - Brucine: Human health tier II assessment

11.10.1 Toxic Combustion Products

... Oxides of nitrogen may form in fires.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

Brucine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain. (L1230)
L1230: Wikipedia. Strychnine. Last Updated 20 July 2009. http://en.wikipedia.org/wiki/Strychnine

12.1.2 Carcinogen Classification

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

12.1.3 Health Effects

Death may result from asphyxia or sheer exhaustion. (L1227)
L1227: Wikipedia. Brucine. Last Updated 8 April 2009. http://en.wikipedia.org/wiki/Brucine

12.1.4 Exposure Routes

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Oral (ingestion) (L1817) ; dermal (L1817)
L1817: Wikipedia. Phytotoxin. Last Updated 7 August 2009. http://en.wikipedia.org/wiki/Phytotoxin

12.1.5 Symptoms

Inhalation Exposure
See Ingestion.
Eye Exposure
Redness.
Ingestion Exposure
Headache. Nausea. Vomiting. Muscle twitching. Restlessness. Convulsions. Laboured breathing.
Brucine causes muscular convulsions of increasing intensity and frequency and eventually death through asphyxia or sheer exhaustion. (L1227)
L1227: Wikipedia. Brucine. Last Updated 8 April 2009. http://en.wikipedia.org/wiki/Brucine

12.1.6 Adverse Effects

Neurotoxin - Other CNS neurotoxin

12.1.7 Acute Effects

12.1.8 Toxicity Data

LD50: 4 mg/kg (Oral, Rat) (T14) LD50: 91 mg/kg (Intraperitoneal, Rat) (T14) LD50: 60 mg/kg (Subcutaneous, Rat) (T14)
T14: Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.

12.1.9 Treatment

Treatment of brucine poisoning involves an oral application of an activated charcoal infusion to absorb any poison within the digestive tract that has not yet been absorbed into the blood. Anticonvulsants such as phenobarbital or diazepam are administered to control convulsions, along with muscle relaxants such as dantrolene to combat muscle rigidity. (L1228)
L1228: Wikipedia. Strychnine poisoning. Last Updated 25 June 2009. http://en.wikipedia.org/wiki/Strychnine_poisoning

12.1.10 Antidote and Emergency Treatment

Basic treatment: Establish a patent airway. 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. Anticipate convulsions and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. Administer activated charcoal ... Use rapid cooling measures to treat hyperthermia. /Strychnine and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 323
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... Treat convulsions with diazepam (Valium) ... Use proparacaine hydrochloride to assist eye irrigation ... /Strychnine and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 323-4

12.1.11 Medical Surveillance

1) Initial Medical Screening: Employees should be screened for history of certain medical conditions ... which might place the employee at incr risk from strychnine exposure. ... Persons with a history of convulsive disorders may be more susceptible to the effects of this agent. 2) Periodic Medical Examination: Any employee developing ... /convulsive disorders/ should be referred for further medical examination. /Strychnine/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1

12.1.12 Human Toxicity Excerpts

CONVULSIONS.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-249
BRUCINE & TETRAMETHYL-AMMONIUM COMPOUNDS IN GENERAL ... PRODUCE PARALYSIS OF THE CURARE TYPE ... THEREFORE, IN ADDITION TO THE CENTRAL EFFECTS, PERIPHERAL PARALYSIS OCCURS, WITH RESPIRATORY FAILURE.
Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 106
/BRUCINE/ ... HAS BEEN SAID TO CAUSE WEAKNESS OF VISION AS THOUGH SEEING THROUGH A FOG, ALONG WITH TINNITUS & HEADACHE. ... IT WAS ... THE IMPRESSION THAT BRUCINE SENSITIZED DISCRIMINATION OF LIGHT & COLOR DIFFERENCES, & INCR VISUAL FIELD FOR COLORS.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 159
BRUCINE IS MUCH LESS POTENT THAN STRYCHNINE.
Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 582
For more Human Toxicity Excerpts (Complete) data for BRUCINE (7 total), please visit the HSDB record page.

12.1.13 Non-Human Toxicity Excerpts

Brucine was evaluated for mutagenicity in the Salmonella/microsome preincubation assay using the standard protocol approved by the National Toxicology Program. Brucine was tested at doses of 0, 33, 100, 333, 1000, 3333, and 6666 ug/plate in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor induced rat or hamster liver S9 /metabolic activation system/. Brucine was negative in these tests and the highest ineffective dose level tested in any Salmonella tester strain was 6666 ug/plate.
Zeiger E et al; Environ Mutagen 9: 1-110 (1987)
Lepomis macrochirus (bluegill sunfish); static bioassay in fresh water at 23 °C, mild aeration applied after 24 hr; material added 63 ppm: % survival after 24 hr, was 0; material added 40 ppm: % survival after 24 hr, 48 hr, 72 hr, & 96 hr was 40, 30, 20, & 20 respectively; material added 32 ppm: % survival after 24 hr, 48 hr, 72 hr & 96 hr was 90, 80, 60, & 40 respectively; material added 25 ppm: % survival after 24 hr, 48 hr, 72 hr, 96 hr was 100.
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 294
Menidia beryllina; static bioassay in synthetic seawater at 23 °C, mild aeration applied after 24 hr; material added 32 ppm: % survival after 24 hr, 48 hr, 72 hr, & 96 hr was 80, 60, 40, & 20 respectively; material added 18 ppm: % survival after 24 hr, 48 hr, 72 hr, & 96 hr was 100, 100, 80, & 70 respectively; material added 10 ppm: % survival after 24 hr, 48 hr, 72 hr & 96 hr was 100, 100, 100, & 90 respectively.
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 294

12.1.14 Non-Human Toxicity Values

LD50 Rabbit oral 4 mg/kg
Sax, N.I. Dangerous Properties of Industrial Materials. 6th ed. New York, NY: Van Nostrand Reinhold, 1984., p. 542
LD50 Rat ip 91 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 533
LD50 Mouse sc 60 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 533

12.1.15 Populations at Special Risk

... Persons with convulsive disorders. /Strychnine/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1

12.2 Ecological Information

12.2.1 Ecotoxicity Values

LC50 Lepomis macrochirus (bluegill sunfish) 36 ppm/96 hr (static bioassay in fresh water @ 23 °C, with mild aeration after 24 hr)
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 294
LC50 Menidia beryllina 20 ppm/96 hr (static bioassay in synthetic seawater @ 23 °C, with mild aeration after 24 hr)
Verschueren, K. Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co., 1983., p. 294

12.2.2 ICSC Environmental Data

The substance is harmful to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to birds.

12.2.3 Environmental Fate / Exposure Summary

Brucine's production and use as chemical intermediate and pharmaceutical may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.0X10-10 mm Hg at 25 °C indicates brucine will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase brucine will be removed from the atmosphere by photolysis or dry deposition. If released to soil, brucine is expected to have high mobility based upon an estimated Koc of 81. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.1X10-16 atm-cu m/mole. Brucine is a basic cmpd and will exist primarily in the ionized form under environmental conditions. Adsorption characteristics of ionic compounds can vary significantly from those of neutral compounds. Therefore, the ability of brucine to adsorb to sediments and soil can not be predicted with certainty since this compound may act markedly different than its estimated Koc value indicates. If released into water, brucine is not expected to adsorb to suspended solids and sediment in water based upon the Koc. Half-life data for brucine in soils are inconclusive with regards to biodegradation loss processes. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. A pKa of 8.28 indicates brucine will exist almost entirely in the ionized form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to occur due to the lack of hydrolyzable functional groups. Occupational exposure to brucine may occur through inhalation of dust particles and dermal contact with this compound at workplaces where brucine is produced or used. The general population may be exposed to brucine via ingestion of pharmaceuticals containing brucine. (SRC)

12.2.4 Artificial Pollution Sources

Brucine may be released to the environment in emissions and aqueous waste stream from its manufacturing facilities and as a hazardous waste disposed of in landfills(SRC).
NIOSH; Current Awareness File (1984)
Brucine's production and use as chemical intermediate(1,2) and pharmaceutical(1) may result in its release to the environment through various waste streams(SRC).
(1) Budavari S; The Merck Index. 12th ed. Whitehouse Station,NJ: Merck and Co., Inc. p. 238 (1996)
(2) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary. 12th ed. NY,NY: Van Nostrand Rheinhold Co. p. 174 (1993)

12.2.5 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that brucine is expected to have high mobility in soil(SRC). However, the ability of brucine to adsorb to sediments and soil can not be predicted with certainty since this compound may act markedly different than its estimated Koc value indicates(SRC). Volatilization of brucine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(3). Brucine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0X10-10 mm Hg(SRC), determined from a fragment constant method(4). Half-life data for brucine indicate that biodegradation in soil may occur(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton, FL: CRC Press (1985)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that brucine is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 8.28 indicates brucine will exist almost entirely in the ionized form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(6) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low.
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 5-4, 5-10, 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(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, Stephen R., consult. ed., Washington, DC: Amer Chem Soc p. 180 (1995)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), brucine, which has an estimated vapor pressure of 1.0X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase brucine may be removed from the air by direct photolysis and dry deposition(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

12.2.6 Environmental Biodegradation

Brucine was incubated for 65 days in the dark at 20 °C at a concn of 180 and 150 ppm in Texas (pH=7.8) and Mississippi (pH= 4.8) soils, with 16% and 12% moisture content(1). Half-lives of 23.1 and 37.1 days, respectively, were noted(1). However, no distinction was made between specific loss mechanisms.
(1) Loehr R; Treatability potential for EPA listed hazardous wastes in soil. Ada,OK: Robert S. Kerr Environ Res Lab. USEPA600/2-89/011 (1989)

12.2.7 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of brucine with photochemically-produced hydroxyl radicals has been estimated as 3.21X10-10 cu cm/molecule-sec at 25 °C(SRC) using an estimation method(1). This corresponds to an atmospheric half-life of about 7 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Based on the structure of brucine, chemical hydrolysis does not appear to be an important fate process at least at neutral pH. The hydrolysis half-life has been estimated as greater than 1 year(SRC). The only functional group which may be susceptible to chemical hydrolysis is the amide group, but half-lives on the average of several years at pH 7 and 25 °C have been reported for amides(3,SRC). The UV absorption spectrum for brucine in methanol and in methanol with HCl added reveals that brucine strongly absorbs UV light wavelength greater than 290 nm(4). These data suggest that brucine has the potential to undergo direct photolysis in the atmosphere, on soil surfaces and in the upper few meters of natural waters where there is light penetration(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Mill T et al; Environmental Fate and Exposure Studies Development of a PC-SAR for Hydrolysis: Esters, Alkyl Halides and Epoxides. EPA Contract No. 68-02-4254. Menlo Park, CA: SRI International (1987)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(4) Sadtler; Standard UV Spectra No. 600 (1966)

12.2.8 Environmental Bioconcentration

An estimated BCF of 3 was calculated for brucine(SRC), using a log Kow of 0.98(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. 180 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 5-4, 5-10 (1990)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.9 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc for brucine can be estimated to be 81(SRC). According to a classification scheme(2), this estimated Koc value suggests that brucine is expected to have high mobility in soil. The pKa of brucine is 8.28(3) indicating that this compound will exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize. Therefore, the ability of brucine to adsorb to sediments an soil cannot be predicted with certainty since this compound may act markedly different than its estimated Koc value indicates(SRC).
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) Lide DR; CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc. p. 8-56 (1998)

12.2.10 Volatilization from Water / Soil

The Henry's Law constant for brucine is estimated as 2.1X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that brucine is expected to be essentially nonvolatile from water surfaces(2). Brucine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0X10-10 mm Hg(SRC), determined from a fragment constant method(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE(eds), Boca Raton, FL: CRC Press (1985)

12.2.11 Plant Concentrations

Brucine is a constituent of the seeds of Strychnos sp. (e.g. S. nuxvomica(1,2), and S. ignatii Berg., Loganiaceae(1)).
(1) Budavari S; The Merck Index. 12th ed. Whitehouse Station,NJ: Merck and Co., Inc. p. 238 (1996)
(2) Young CT; Kirk-Othmer Encycl Chem Tech 4th. NY,NY: Wiley Interscience 17: 555 (1996)

12.2.12 Probable Routes of Human Exposure

... By ingestion & inhalation.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 174
NIOSH (NOES Survey 1981-1983) has statistically estimated that 335 workers (119 of these are female) are potentially exposed to brucine in the USA(1). Occupational exposure to brucine may occur through inhalation and dermal contact with this compound at workplaces where brucine is produced or used(SRC). The general population may be exposed to brucine via ingestion of pharmaceuticals containing brucine(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Nature Journal References

14.7 Chemical Co-Occurrences in Literature

14.8 Chemical-Gene Co-Occurrences in Literature

14.9 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 KEGG: Phytochemical Compounds

19.5 KEGG: Natural Toxins

19.6 ChemIDplus

19.7 CAMEO Chemicals

19.8 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

19.9 ChEMBL Target Tree

19.10 UN GHS Classification

19.11 CCSBase Classification

19.12 EPA DSSTox Classification

19.13 EPA TSCA and CDR Classification

19.14 LOTUS Tree

19.15 EPA Substance Registry Services Tree

19.16 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
    LICENSE
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    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA Chemicals under the TSCA
    Strychnidin-10-one, 2,3-dimethoxy-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Hazardous Substances Data Bank (HSDB)
  10. ILO-WHO International Chemical Safety Cards (ICSCs)
  11. New Zealand Environmental Protection Authority (EPA)
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    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  12. NJDOH RTK Hazardous Substance List
  13. Emergency Response Guidebook (ERG)
  14. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://haz-map.com/About
  15. ChEBI
  16. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  17. Toxin and Toxin Target Database (T3DB)
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    http://www.t3db.ca/downloads
  18. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  19. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  20. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  21. Drug Gene Interaction database (DGIdb)
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    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
    AC-C[CYS-GLU-HIS-D-PHE-ARG-TRP-D-CYS]-PRO-PRO-LYS-ASP-NH2
    https://www.dgidb.org/drugs/iuphar.ligand:1342
  22. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  23. Therapeutic Target Database (TTD)
  24. Cosmetic Ingredient Review (CIR)
  25. Crystallography Open Database (COD)
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    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  26. The Cambridge Structural Database
  27. Hazardous Chemical Information System (HCIS), Safe Work Australia
  28. NITE-CMC
  29. IUPAC Digitized pKa Dataset
  30. NMRShiftDB
  31. Japan Chemical Substance Dictionary (Nikkaji)
  32. KEGG
    LICENSE
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    https://www.kegg.jp/kegg/legal.html
  33. Natural Product Activity and Species Source (NPASS)
  34. MassBank Europe
  35. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  36. Metabolomics Workbench
  37. Nature Chemical Biology
  38. Nature Chemistry
  39. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  40. Pharos
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    https://pharos.nih.gov/about
  41. SpectraBase
    2,3-Dimethoxystrychnidin-10-one
    https://spectrabase.com/spectrum/4URmTPfOqzI
    2,3-Dimethoxystrychnidin-10-one
    https://spectrabase.com/spectrum/8IKRD80wzfj
  42. Springer Nature
  43. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  44. Wikidata
  45. Wikipedia
  46. Wiley
  47. PubChem
  48. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  49. GHS Classification (UNECE)
  50. EPA Substance Registry Services
  51. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  52. PATENTSCOPE (WIPO)
  53. NCBI
CONTENTS