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N,N,N-trimethylglycinium

PubChem CID
248
Structure
N,N,N-trimethylglycinium_small.png
N,N,N-trimethylglycinium_3D_Structure.png
Molecular Formula
Synonyms
  • TRIMETHYL GLYCINE
  • N,N,N-trimethylglycinium
  • Cystadane
  • carboxymethyl(trimethyl)azanium
  • carboxy-N,N,N-trimethylmethanaminium
Molecular Weight
118.15 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2024-12-27
Description
N,N,N-trimethylglycinium is a quaternary ammonium ion in which the substituents on nitrogen are methyl (three) and carboxymethyl. It has a role as a fundamental metabolite. It is a conjugate acid of a glycine betaine.
A naturally occurring compound that has been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1341)
BETAINE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1996 and is indicated for homocystinuria and unipolar depression and has 7 investigational indications.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N,N,N-trimethylglycinium.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

carboxymethyl(trimethyl)azanium
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KWIUHFFTVRNATP-UHFFFAOYSA-O
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[N+](C)(C)CC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C5H12NO2+
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

6640-00-2
6915-17-9

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DrugBank ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 NSC Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Acidin Pepsin
  • Acidin-Pepsin
  • AcidinPepsin
  • Betaine
  • Betaine Hydrochloride
  • Betaine, Glycine
  • C.B.B.
  • Citrate de Bétaïne Beaufour
  • Citrate de Bétaïne UPSA
  • Cystadane
  • Glycine Betaine
  • Hepastyl
  • Hydrochloride, Betaine
  • Lycine
  • Novobetaine
  • Oxyneurine
  • Scorbo bétaïne
  • Scorbo-bétaïne
  • Scorbobétaïne
  • Stea 16
  • Stea-16
  • Stea16

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
118.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
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
118.086803626 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
118.086803626 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
1
Reference
Computed by PubChem
Property Name
Complexity
Property Value
93.1
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

Solid

3.2.2 Melting Point

293 - 301 °C

3.2.3 Solubility

611.0 mg/mL at 19 °C

3.2.4 Collision Cross Section

133.8 Ų [M+Na]+

121.1 Ų [M+H]+

130.4 Ų [M+K]+

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.3.1.1 Human Drugs
Human drug -> Prescription

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
View All
Spectra ID
Frequency
500 MHz
Solvent
H2O
Shifts [ppm]
3.25, 3.89
Thumbnail
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2 of 4
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Spectra ID
Frequency
500 MHz
Solvent
H2O
Shifts [ppm]
3.89, 3.25
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 4
View All
Spectra ID
Frequency
400 MHz
Solvent
H2O
Shifts [ppm]
56.07, 68.93, 171.84
Thumbnail
Thumbnail
2 of 4
View All
Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
-0.00:3.11, 68.93:12.82, 56.07:37.77, 171.84:5.43
Thumbnail
Thumbnail

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)
3.25:3.24, 3.25:3.26, 3.89:3.87, 3.25:3.89, 3.44:3.44, 3.25:3.28, 3.33:3.24, 3.26:3.29, 3.89:3.92, 3.89:3.89, 3.21:3.25
Thumbnail
Thumbnail

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
3.89:68.64:0.18, 3.25:55.86:1.00
Thumbnail
Thumbnail

4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 4
View All
NIST Number
230757
Library
Main library
Total Peaks
75
m/z Top Peak
58
m/z 2nd Highest
44
m/z 3rd Highest
42
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
33359
Library
Replicate library
Total Peaks
32
m/z Top Peak
58
m/z 2nd Highest
42
m/z 3rd Highest
44
Thumbnail
Thumbnail

4.3.2 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

118.024 100

59.049 7.61

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

58.26 100

59.337 50.77

117.939 8.65

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

4.3.3 LC-MS

1 of 5
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
10 eV
Fragmentation Mode
CID
Column Name
Shimadzu Shim-Pack XR-ODS III; C18; 2.2um; 80A; 2.0x150mm
Precursor Adduct
[M]+
Top 5 Peaks

118.086 999

119.0894 76

Thumbnail
Thumbnail
License
CC BY
2 of 5
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]+
Top 5 Peaks

118.0862 999

119.0896 81

Thumbnail
Thumbnail
License
CC BY

4.3.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M]+
Precursor m/z
118.086255
Ionization Mode
positive
Retention Time
9.821421753
Top 5 Peaks

59.072678 0.59

58.06487 0.41

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[2M+H]+
Precursor m/z
235.1652
Ionization
ESI
Ionization Mode
positive
Collision Energy
30.0,50.0,70.0
Retention Time
5.75226
Top 5 Peaks

118.0861 100

59.0728 4

58.0650 3.70

Thumbnail
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.2.2 EU Clinical Trials Register

7.3 Biomarker Information

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Gastrointestinal Agents
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)
Lipotropic Agents
Endogenous factors or drugs that increase the transport and metabolism of LIPIDS including the synthesis of LIPOPROTEINS by the LIVER and their uptake by extrahepatic tissues. (See all compounds classified as Lipotropic Agents.)

8.2 Human Metabolite Information

8.2.1 Tissue Locations

  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis

8.2.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Mitochondria

8.2.3 Metabolite Pathways

8.3 Biochemical Reactions

9 Associated Disorders and Diseases

Disease
Chronic renal failure
References
Disease
Continuous ambulatory peritoneal dialysis
References
Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Early preeclampsia
References
PubMed: 22494326
Disease
Pregnancy
References

PubMed: 3252730, 663967, 12833386, 2994907, 17704099, 12698507, 17061063, 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
Late-onset preeclampsia
References
PubMed: 23159745
Disease
Hypermethioninemia
References
Disease
Perillyl alcohol administration for cancer treatment
References
Disease
Pancreatic cancer
References
Disease
Periodontal disease
References
PubMed: 20300169
Disease
Frontotemporal dementia
References
PubMed: 23857558
Disease
Lewy body disease
References
PubMed: 23857558
Disease
Lung Cancer
References
Disease
Argininosuccinic aciduria
References

PubMed: 5075233, 19551947, 12408190

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

Disease
Propionic acidemia
References

PubMed: 19809936, 19551947, 2226555, 28853722

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

Disease
Phenylketonuria
References

PubMed: 7333014, 2091926, 12101068, 17574536, 6790852, 466810, 2116554, 19551947, 25964343, 15168722, 4837567

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

Disease
Maple syrup urine disease
References

PubMed: 12101068, 10508118, 10472531, 19551947, 11978597, 10234605, 6422161, 23430924, 18088602

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

Peritoneal dialysis in maple-syrup-urine disease: Studies on branched-chain amino and keto acids. Eur J Pediatr (1980) 134: 57. https://doi.org/10.1007/BF00442404

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart
Disease
Dimethylglycine Dehydrogenase Deficiency
References
PubMed: 10102904

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Thieme References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Protein Bound 3D Structures

12.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

12.2 Chemical-Target Interactions

12.3 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChEMBL Target Tree

15.4 NORMAN Suspect List Exchange Classification

15.5 EPA DSSTox Classification

15.6 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. ChEBI
  2. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  3. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  4. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  5. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  6. Crystallography Open Database (COD)
    LICENSE
    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/
  7. Drugs@FDA
    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.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  9. EPA DSSTox
    Carboxy-N,N,N-trimethylmethanaminium
    https://comptox.epa.gov/dashboard/DTXSID40859190
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. Human Metabolome Database (HMDB)
    LICENSE
    HMDB 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 (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  11. EU Clinical Trials Register
  12. SpectraBase
  13. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  16. MassBank Europe
  17. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  18. Metabolomics Workbench
  19. Natural Product Activity and Species Source (NPASS)
  20. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    BETAINE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  21. Protein Data Bank in Europe (PDBe)
  22. RCSB Protein Data Bank (RCSB PDB)
    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
  23. 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/
  24. Wikidata
  25. 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
  26. PubChem
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
  29. NCBI
CONTENTS