Metabolite Card

Formula: C3H9N (59.0735)
SMILES: CN(C)C

Synonyms [en]

trimethylamine; (CH3)3N; N,N-dimethylmethanamine; tridimethylaminomethane; N(CH3)3; Trimethylamin

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Trimethylamine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000018859). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 degree centigrade and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid. Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath. It is also associated with taking large doses of choline. Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. Trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell. Trimethylamine in the urine is a biomarker for the consumption of legumes. It has also been found to be a product of various types of bacteria, such as Achromobacter, Acinetobacter, Actinobacteria, Aeromonas, Alcaligenes, Alteromonas, Anaerococcus, Bacillus, Bacteroides, Bacteroidetes, Burkholderia, Campylobacter, Citrobacter, Clostridium, Desulfitobacterium, Desulfovibrio, Desulfuromonas, Edwardsiella, Enterobacter, Enterococcus, Escherichia, Eubacterium, Firmicutes, Flavobacterium, Gammaproteobacteria, Haloanaerobacter, Klebsiella, Micrococcus, Mobiluncus, Olsenella, Photobacterium, Proteobacteria, Proteus, Providencia, Pseudomonas, Rhodopseudomonas, Ruminococcus, Salmonella, Sarcina, Serratia, Shewanella, Shigella, Sinorhizobium, Sporomusa, Staphylococcus, Stigmatella, Streptococcus, Vibrio and Yokenella (PMID:26687352; PMID:25108210; PMID:24909875; PMID:28506279; PMID:27190056). Trimethylamine is a marker for urinary tract infection brought on by E. coli. (PMID:25108210; PMID:24909875). It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 75-50-3
  • PubChem: 1146
  • ChEBI: ChEBI:18139
  • HMDB: HMDB0000906
  • KEGG: C00565
  • BioCyc: TRIMETHYLAMINE
  • NCBI MeSH: trimethylamine
  • Wikipedia: Trimethylamine
  • RefMet: RM0136020
  • MoNA: HMDB0000906_c_ms_99629
  • MoNA: HMDB0000906_ms_ms_1292
  • MoNA: HMDB0000906_ms_ms_1293
  • MoNA: HMDB0000906_ms_ms_1294
  • MoNA: JP009052
  • MoNA: MoNA002178
  • MoNA: MoNA002179
  • MoNA: MoNA002181
  • Metlin: METLIN_3772
  • Coconut NaturalProduct: CNP0522907.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02511 1.5.8.2 trimethylamine:electron-transferring flavoprotein oxidoreductase(demethylating)
KEGG:R02560 1.7.2.3 trimethylamine:cytochrome c oxidoreductase
KEGG:R04877 C05570<=>C05571 + C00565
KEGG:R05623 1.14.13.148 N,N,N-trimethylamine,NADPH:oxygen oxidoreductase (N-oxide-forming)
KEGG:R07228 1.21.4.4 acetyl-phosphate trimethylamine:thioredoxin disulfide oxidoreductase (N,N,N-trimethylglycine-forming)
KEGG:R09124 2.1.1.247 trimethylamine:coenzyme M methyltransferase
KEGG:R10016 2.1.1.250 trimethylamine:[Co(I) corrinoid protein] Co-methyltransferase
KEGG:R10017 2.1.1.252 tetramethylammonium:[Co(I) corrinoid protein] Co-methyltransferase
KEGG:R10285 4.3.99.4 choline trimethylamine-lyase (acetaldehyde-forming)
KEGG:R11875 1.14.13.239 L-carnitine,NADH:oxygen oxidoreductase (trimethylamine-forming)
KEGG:R11911 1.14.13.239 L-carnitine,NADPH:oxygen oxidoreductase (trimethylamine-forming)
BioCyc:RXN-5921 1.14.13.239 CARNITINE + OXYGEN-MOLECULE + NADH-P-OR-NOP + PROTON --> CPD-16618 + TRIMETHYLAMINE + NAD-P-OR-NOP + WATER
BioCyc:RXN-18258 1.14.13.239 GAMMA-BUTYROBETAINE + OXYGEN-MOLECULE + NADH-P-OR-NOP + PROTON --> SUCC-S-ALD + TRIMETHYLAMINE + NAD-P-OR-NOP + WATER
BioCyc:1.7.2.3-RXN 1.7.2.3 TRIMETHYLAMINE-N-O + 2 Cytochromes-C-Reduced + 3 PROTON --> TRIMETHYLAMINE + 2 Cytochromes-C-Oxidized + WATER
BioCyc:RXN-19619 1.7.2.3 TRIMETHYLAMINE-N-O + 2 A-REDUCED-TORY-PROTEIN + 3 PROTON --> TRIMETHYLAMINE + 2 an-oxidized-TorY-protein + WATER
BioCyc:RXN0-5264 Trimethylamine-N-oxide reductase (menaquinone)
BioCyc:RXN-18376 1.14.13.239 CHOLINE + OXYGEN-MOLECULE + NADH-P-OR-NOP + PROTON --> GLYCOLALDEHYDE + TRIMETHYLAMINE + NAD-P-OR-NOP + WATER
BioCyc:RXN0-5263 TRIMETHYLAMINE-N-O + 3 PROTON + 2 E- --> TRIMETHYLAMINE + WATER
BioCyc:RXN-19618 1.7.2.3 TRIMETHYLAMINE-N-O + 2 a-reduced-TorC-protein + 3 PROTON --> TRIMETHYLAMINE + 2 an-oxidized-TorC-protein + WATER
BioCyc:RXN-12900 1.14.13.148 TRIMETHYLAMINE + OXYGEN-MOLECULE + NADPH --> TRIMETHYLAMINE-N-O + WATER + NADP
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Organism Source

Taxonomy Source

  1. Asarum europaeum [ncbi taxid: 49456]
  2. Asarum sieboldii [ncbi taxid: 76098]
  3. Astragalus oxyphysus [ncbi taxid: 90201]
  4. Bupleurum chinense [ncbi taxid: 52451]
  5. Bupleurum falcatum [ncbi taxid: 46367]
  6. Bupleurum scorzonerifolium [ncbi taxid: 48105]
  7. Buthus martensi [ncbi taxid: ]
  8. Buthus martensii [ncbi taxid: ]
  9. Calceolaria andina [ncbi taxid: 2304407]
  10. Centaurea glastifolia [ncbi taxid: 75647]
  11. Clavaria pyxidata [ncbi taxid: ]
  12. Cucumaria okhotensis [ncbi taxid: ]
  13. Cuscuta reflexa [ncbi taxid: 4129]
  14. Escherichia coli [ncbi taxid: 562]
  15. Euphorbia armena [ncbi taxid: ]
  16. FOOD SAKE [ncbi taxid: ]
  17. Galanthus nivalis [ncbi taxid: 4670]
  18. Grindelia havardii [ncbi taxid: 1114740]
  19. Homo sapiens [ncbi taxid: 9606]
  20. Homo sapiens (Exhaled breath) [ncbi taxid: ]
  21. Hydrodictyon reticulatum [ncbi taxid: 3107]
  22. Ligusticum chuanxiong [ncbi taxid: 2689076]
  23. Ligusticum chuanxiung [ncbi taxid: ]
  24. Ligusticum sinense [ncbi taxid: ]
  25. Lobaria laetevirens [ncbi taxid: ]
  26. Mercurialis annua L. [ncbi taxid: ]
  27. Mercurialis ovata Sternb. & Hoppe [ncbi taxid: ]
  28. Mercurialis perennis L. [ncbi taxid: ]
  29. Mesobuthus martensii [ncbi taxid: ]
  30. Nephelium maingayi [ncbi taxid: 1277290]
  31. Oenanthe phellandrium [ncbi taxid: ]
  32. Parapristipoma trilineatum [ncbi taxid: 360507]
  33. Plantago depressa [ncbi taxid: 411227]
  34. Polyscias scutellaria [ncbi taxid: 150539]
  35. Prunus dulcis [ncbi taxid: 3755]
  36. Pyrus pyraster [ncbi taxid: 356590]
  37. Semen astragali complanati [ncbi taxid: ]
  38. Senecio candollei [ncbi taxid: 462509]
  39. Sticta fuliginosa [ncbi taxid: 161976]
  40. Sticta sylvatica [ncbi taxid: 1161060]

Pathway Synthetic

pathway id name
PathBank:SMP0001903 N-Oxide Electron Transfer
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-211945 Phase I - Functionalization of compounds
Reactome:R-CEL-211859 Biological oxidations
Reactome:R-CFA-1430728 Metabolism
Reactome:R-HSA-211859 Biological oxidations
Reactome:R-HSA-217271 FMO oxidises nucleophiles
Reactome:R-HSA-1643685 Disease
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-211859 Biological oxidations
Reactome:R-MMU-217271 FMO oxidises nucleophiles
Reactome:R-RNO-211945 Phase I - Functionalization of compounds
Reactome:R-SSC-211945 Phase I - Functionalization of compounds
Reactome:R-BTA-211859 Biological oxidations
Reactome:R-BTA-217271 FMO oxidises nucleophiles
Reactome:R-CEL-217271 FMO oxidises nucleophiles
Reactome:R-DRE-211945 Phase I - Functionalization of compounds
Reactome:R-RNO-211859 Biological oxidations
Reactome:R-RNO-217271 FMO oxidises nucleophiles
Reactome:R-SSC-1430728 Metabolism
View All Pathways