|Preferred IUPAC name
(Trimethyl)amine (The name trimethylamine is deprecated.)
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||59.112 g·mol−1|
|Density||670 kg m−3 (at 0 °C)|
627.0 kg m−3 (at 25 °C)
|Melting point||−117.20 °C; −178.96 °F; 155.95 K|
|Boiling point||3 to 7 °C; 37 to 44 °F; 276 to 280 K|
|Vapor pressure||188.7 kPa (at 20 °C)|
|95 μmol Pa−1 kg−1|
Std enthalpy of
|−24.5 to −23.0 kJ mol−1|
|GHS signal word||DANGER|
|H220, H315, H318, H332, H335|
|P210, P261, P280, P305+351+338|
|Flash point||−7 °C (19 °F; 266 K)|
|190 °C (374 °F; 463 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|500 mg kg−1 (oral, rat)|
|US health exposure limits (NIOSH):|
|TWA 10 ppm (24 mg/m3) ST 15 ppm (36 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations. It is a toxic compound which causes corrosion and necrosis after contact with mucous membranes. It is a gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in water. TMA is a nitrogenous base and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.
Trimethylamine is a product of decomposition of plants and animals. In humans, it is synthesized exclusively by gut microbiota from dietary nutrients such as choline and carnitine. High levels of trimethylamine are associated with the development of fish odor syndrome, which arise from the foul, fishy odor of trimethylamine. TMA is the substance mainly responsible for the odor often associated with rotting fish, some infections, bad breath and can be a cause of vaginal odor due to bacterial vaginosis. It is also associated with taking large doses of choline and carnitine.
In 2013, trimethylamine was identified as a potent full agonist of human TAAR5, a trace amine-associated receptor that is expressed in the olfactory epithelium and functions as an olfactory receptor for tertiary amines. One or more additional odorant receptors appear to be involved in trimethylamine olfaction in humans as well.
- 3 CH3OH + NH3 → (CH3)3N + 3 H2O
- 9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2↑
Acute and chronic toxic effects of TMA were suggested in medical literature as early as the 19th century. TMA causes eye and skin irritation, and it is suggested to be a uremic toxin. In patients, trimethylamine caused stomach ache, vomiting, diarrhoea, lacrimation, greying of the skin and agitation. Apart from that, reproductive/developmental toxicity has been reported.
Due to toxicity and widespread use of TMA in industry, several guidelines with exposure limit for workers are available e.g. the Recommendation from the Scientific Committee on Occupational Exposure Limits by the European Union Commission.
Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators or herbicides, strongly basic anion exchange resins, dye leveling agents and a number of basic dyes. Gas sensors to test for fish freshness detect trimethylamine.
Trimethylaminuria is an autosomal recessive genetic disorder involving a defect in the function or expression of flavin-containing monooxygenase 3 (FMO3) which results in poor trimethylamine metabolism. Individuals with trimethylaminuria develop a characteristic fish odor—the smell of trimethylamine—in their sweat, urine, and breath after the consumption of choline-rich foods. A condition similar to trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell, especially after eating food containing a high proportion of rapeseed.
- Merck Index, 11th Edition, 9625.
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- Falony G, Vieira-Silva S, Raes J (2015). "Microbiology Meets Big Data: The Case of Gut Microbiota-Derived Trimethylamine". Annu. Rev. Microbiol. 69: 305–321. doi:10.1146/annurev-micro-091014-104422. PMID 26274026.
we review literature on trimethylamine (TMA), a microbiota-generated metabolite linked to atherosclerosis development.
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Trimethylamine is exclusively a microbiota-derived product of nutrients (lecithin, choline, TMAO, L-carnitine) from normal diet, from which seems originate two diseases, trimethylaminuria (or Fish-Odor Syndrome) and cardiovascular disease through the proatherogenic property of its oxidized liver-derived form.
- Wallrabenstein I, Kuklan J, Weber L, Zborala S, Werner M, Altmüller J, Becker C, Schmidt A, Hatt H, Hummel T, Gisselmann G (2013). "Human trace amine-associated receptor TAAR5 can be activated by trimethylamine". PLoS ONE. 8 (2): e54950. Bibcode:2013PLoSO...854950W. doi:10.1371/journal.pone.0054950. PMC 3564852. PMID 23393561.
- Zhang J, Pacifico R, Cawley D, Feinstein P, Bozza T (February 2013). "Ultrasensitive detection of amines by a trace amine-associated receptor". J. Neurosci. 33 (7): 3228–39. doi:10.1523/JNEUROSCI.4299-12.2013. PMC 3711460. PMID 23407976.
We show that [human TAAR5] responds to the tertiary amine N,N-dimethylethylamine and to a lesser extent to trimethylamine, a structurally related agonist for mouse and rat TAAR5 (Liberles and Buck, 2006; Staubert et al., 2010; Ferrero et al., 2012).
- Zhang LS, Davies SS (April 2016). "Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions". Genome Med. 8 (1): 46. doi:10.1186/s13073-016-0296-x. PMC 4840492. PMID 27102537.
Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
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- Roger Adams, B. K. Brown. "Trimethylamine". Organic Syntheses.; Collective Volume, 1, p. 75
- Wills, M.R.; Savory, J. Biochemistry of renal failure. Ann Clin Lab Sci 1981, 11, 292-299.
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- European Commission. Directorate-General for Employment, Social Affairs and Inclusion. Scientific Committee on Occupational Exposure Limits. (2017). SCOEL/REC/179 trimethylamine recommendation from the Scientific Committee on Occupational Exposure Limits. Publications Office. OCLC 1032584642.
- Jaworska, Kinga; Bielinska, Klaudia; Gawrys-Kopczynska, Marta; Ufnal, Marcin (27 August 2019). "TMA (trimethylamine), but not its oxide TMAO (trimethylamine-oxide), exerts hemodynamic effects - implications for interpretation of cardiovascular actions of gut microbiome". Cardiovascular Research. doi:10.1093/cvr/cvz231. ISSN 0008-6363.
- Jaworska, Kinga; Hering, Dagmara; Mosieniak, Grażyna; Bielak-Zmijewska, Anna; Pilz, Marta; Konwerski, Michał; Gasecka, Aleksandra; Kapłon-Cieślicka, Agnieszka; Filipiak, Krzysztof (26 August 2019). "TMA, A Forgotten Uremic Toxin, but Not TMAO, Is Involved in Cardiovascular Pathology". Toxins. 11 (9): 490. doi:10.3390/toxins11090490. ISSN 2072-6651.
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- Pearson, Arthur W.; Butler, Edward J.; Curtis, R. Frank; Fenwick, G. Roger; Hobson-Frohock, Anthony; Land, Derek G. (1979). "Effect of rapeseed meal on trimethylamine metabolism in the domestic fowl in relation to egg taint". Journal of the Science of Food and Agriculture. 30 (8): 799–804. doi:10.1002/jsfa.2740300809.
- Lichovníková, M.; Zeman, L.; Jandásek, J. (2008). "The effect of feeding untreated rapeseed and iodine supplement on egg quality" (PDF). Czech Journal of Animal Science. 53 (2): 77–82. Retrieved 19 December 2016.
- Molecule of the Month: Trimethylamine
- NIST Webbook data
- CDC - NIOSH Pocket Guide to Chemical Hazards
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