Record Information
Version2.0
Creation Date2012-05-31 13:02:02 -0600
Update Date2015-09-13 15:15:20 -0600
Secondary Accession Numbers
  • ECMDB00906
Identification
Name:Trimethylamine
Description: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
Structure
Thumb
Synonyms:
  • (CH3)3N
  • (CH3)3NH
  • (CH3)3NH+
  • Dimethylmethaneamine
  • N,N-Dimethyl-Methanamine
  • N,N-Dimethyl-Methanamine (9CI)
  • N,N-Dimethyl-Methylamine
  • N,N-Dimethylmethanamine
  • N-Trimethylamine
  • TMA
  • TMeAla
  • Trimethylamine
  • Trimethylamine (8CI)
  • Trimethylamine (anhydrous)
  • Trimethylamine anhydrous
  • Trimethylamine anhydrous [UN1083] [Flammable gas]
  • Trimethylamine aqueous solution
  • Trimethylamine aqueous solutions not >50% trimethylamine by mass [UN1297] [Flammable liquid]
  • Trimethylamine for synthesis
  • Trimethylamine HCL
  • Trimethylamine hydrochloride
  • Trimethylamine in aqueous solution
  • Trimethylamine solution
  • Trimethylamine solution (30% or less)
  • Trimethylammonium chloride
Chemical Formula:C3H9N
Weight:Average: 59.1103
Monoisotopic: 59.073499293
InChI Key:GETQZCLCWQTVFV-UHFFFAOYSA-N
InChI:InChI=1S/C3H9N/c1-4(2)3/h1-3H3
CAS number:75-50-3
IUPAC Name:trimethylamine
Traditional IUPAC Name:trimethylamine
SMILES:CN(C)C
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentTrialkylamines
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:1
Melting point:-117.1 °C
Experimental Properties:
PropertyValueSource
Water Solubility:890.0 mg/ml [SCHWEIZER,AE et al. (1978)]PhysProp
LogP:0.314PhysProp
Predicted Properties
PropertyValueSource
Water Solubility654.0 mg/mLALOGPS
logP-0.14ALOGPS
logP0.19ChemAxon
logS1.04ALOGPS
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.99 m3·mol-1ChemAxon
Polarizability7.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 Pw001891Pw001891 greyscalePw001891 simple
N-oxide electron transferPW001889 Pw001889Pw001889 greyscalePw001889 simple
KEGG Pathways:
  • Methane metabolism ec00680
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
  • NADH to trimethylamine N-oxide electron transfer PWY0-1347
  • formate to trimethylamine N-oxide electron transfer PWY0-1355
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-83029e23f5cbd6a60765View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-ed35409515031a3b1b98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-902429fa0e6ccf9ef725View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4i-9000000000-55145d7583823742b4d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-909841d5aea15e062470View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Al-Waiz M, Ayesh R, Mitchell SC, Idle JR, Smith RL: A genetic polymorphism of the N-oxidation of trimethylamine in humans. Clin Pharmacol Ther. 1987 Nov;42(5):588-94. Pubmed: 3677545
  • Chao CK, Zeisel SH: Formation of trimethylamine from dietary choline by Streptococcus sanguis I, which colonizes the mouth. J Nutr Biochem. 1990 Feb;1(2):89-97. Pubmed: 15539190
  • Dzik-Jurasz AS, Prescot AP, Leach MO, Collins DJ: Non-invasive study of human gall bladder bile in vivo using (1)H-MR spectroscopy. Br J Radiol. 2003 Jul;76(907):483-6. Pubmed: 12857709
  • Hillier SL: Diagnostic microbiology of bacterial vaginosis. Am J Obstet Gynecol. 1993 Aug;169(2 Pt 2):455-9. Pubmed: 8357044
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kenyon S, Carmichael PL, Khalaque S, Panchal S, Waring R, Harris R, Smith RL, Mitchell SC: The passage of trimethylamine across rat and human skin. Food Chem Toxicol. 2004 Oct;42(10):1619-28. Pubmed: 15304308
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Leys D, Basran J, Talfournier F, Chohan KK, Munro AW, Sutcliffe MJ, Scrutton NS: Flavin radicals, conformational sampling and robust design principles in interprotein electron transfer: the trimethylamine dehydrogenase-electron-transferring flavoprotein complex. Biochem Soc Symp. 2004;(71):1-14. Pubmed: 15777008
  • Maschke S, Wahl A, Azaroual N, Boulet O, Crunelle V, Imbenotte M, Foulard M, Vermeersch G, Lhermitte M: 1H-NMR analysis of trimethylamine in urine for the diagnosis of fish-odour syndrome. Clin Chim Acta. 1997 Jul 25;263(2):139-46. Pubmed: 9246418
  • Mitchell SC, Zhang AQ, Barrett T, Ayesh R, Smith RL: Studies on the discontinuous N-oxidation of trimethylamine among Jordanian, Ecuadorian and New Guinean populations. Pharmacogenetics. 1997 Feb;7(1):45-50. Pubmed: 9110361
  • Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. Pubmed: 7762816
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
  • Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. Pubmed: 9429235
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Zeisel SH, daCosta KA, LaMont JT: Mono-, di- and trimethylamine in human gastric fluid: potential substrates for nitrosodimethylamine formation. Carcinogenesis. 1988 Jan;9(1):179-81. Pubmed: 3335043
Synthesis Reference:Hirohata, Saneo; Tanba, Kiyonobu; Inoue, Kenichi. Preparation of trimethylamine by zeolite-catalyzed reaction of methanol and ammonia. Jpn. Kokai Tokkyo Koho (2006), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18139
HMDB IDHMDB00906
Pubchem Compound ID1146
Kegg IDC00565
ChemSpider ID1114
WikipediaTrimethylamine
BioCyc IDTRIMETHYLAMINE
EcoCyc IDTRIMETHYLAMINE
Ligand ExpoKEN

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfG
Uniprot ID:
P0AAJ1
Molecular weight:
22752
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. Allows E.coli to grow anaerobically on Me(2)SO as respiratory oxidant
Gene Name:
dmsA
Uniprot ID:
P18775
Molecular weight:
90398
Reactions
Dimethylsulfide + menaquinone + H(2)O = dimethylsulfoxide + menaquinol.
General function:
Involved in electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
dmsB
Uniprot ID:
P18776
Molecular weight:
22869
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfE
Uniprot ID:
P77374
Molecular weight:
89779
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
ynfF
Uniprot ID:
P77783
Molecular weight:
89986
General function:
Involved in oxidoreductase activity
Specific function:
Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions. Can also reduce other N- and S-oxide compounds such as 4-methylmorpholine-N-oxide and biotin sulfoxide (BSO), but with a lower catalytic efficiency
Gene Name:
torZ
Uniprot ID:
P46923
Molecular weight:
88964
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+).
General function:
Involved in iron ion binding
Specific function:
Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torZ. Required for electron transfer to the torZ terminal enzyme
Gene Name:
torY
Uniprot ID:
P52005
Molecular weight:
40286
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. DmsC anchors the dmsAB dimer to the membrane and stabilizes it
Gene Name:
dmsC
Uniprot ID:
P18777
Molecular weight:
30826
General function:
Involved in oxidoreductase activity
Specific function:
Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions
Gene Name:
torA
Uniprot ID:
P33225
Molecular weight:
94455
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+).
General function:
Involved in iron ion binding
Specific function:
Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torA. Acts by transferring electrons from the membranous menaquinones to torA. This transfer probably involves an electron transfer pathway from menaquinones to the N-terminal domain of torC, then from the N-terminus to the C-terminus, and finally to torA. TorC apocytochrome negatively autoregulates the torCAD operon probably by inhibiting the torS kinase activity
Gene Name:
torC
Uniprot ID:
P33226
Molecular weight:
43606
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. The C subunit anchors the other two subunits to the membrane and stabilize the catalytic subunits
Gene Name:
ynfH
Uniprot ID:
P76173
Molecular weight:
30523

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368