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| Solubility = Miscible
| LogP = 0.119
| VaporPressure = 188.7 kPa (at 20 °C)<ref name="Swift">{{cite journal |
| HenryConstant = 95 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
| pKb = 4.19
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'''Trimethylamine''' ('''TMA''') is an [[organic compound]] with the formula N(CH<sub>3</sub>)<sub>3</sub>. It is a colorless, [[hygroscopic]], and flammable [[tertiary amine]]. It is a gas at room temperature but is usually sold as a 40% [[Solution (chemistry)|solution]] in [[Water (molecule)|water]]. (It is also sold in pressurized [[gas cylinder]]s.) TMA is a [[nitrogenous base]] and can be readily [[Protonation|protonated]] to give the 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.
TMA is widely used in industry: it is used in the synthesis of [[choline]], [[tetramethylammonium hydroxide]], [[plant growth regulator]]s or [[herbicide]]s, strongly basic [[ion exchange resin|anion exchange resins]], [[dye]] leveling agents, and a number of basic dyes.<ref name=Ullmann/><ref>{{cite book|title=Ashford's Dictionary of Industrial Chemicals|edition=3rd|year= 2011| page =9362|isbn=978-0-9522674-3-0|last1=Ashford|first1=Robert D.}}</ref> At higher concentrations it has an [[ammonia]]-like odor, and can cause [[necrosis]] of [[mucous membrane]]s on contact.<ref name=":0">{{Citation|chapter=Trimethylamine [MAK Value Documentation, 1983]|date=2014-10-27|pages=1–9|publisher=Wiley-VCH Verlag GmbH & Co. KGaA|isbn=978-3527600410|doi=10.1002/3527600418.mb7550e0914|title=The MAK-Collection for Occupational Health and Safety|doi-access=free}}</ref> At lower concentrations, it has a "fishy" odor, the odor associated with rotting [[fish]].
In humans, ingestion of certain plant and animal (e.g., red meat, egg yolk) food containing [[lecithin]], [[choline]] and [[L-carnitine]] provides certain [[gut microbiota]] with the substrate to synthesize TMA, which is then absorbed into the bloodstream.<ref name="TMA" /><ref name="TMA diseases" /> High levels of trimethylamine in the body are associated with the development of trimethylaminuria, or [[fish odor syndrome]], caused by a genetic defect in the enzyme which degrades TMA; or by taking large doses of supplements containing [[choline]] or [[L-carnitine]].<ref name="TMA">{{cite journal | vauthors = Falony G, Vieira-Silva S, Raes J | title = Microbiology Meets Big Data: The Case of Gut Microbiota-Derived Trimethylamine | journal = Annu. Rev. Microbiol. | volume = 69 | pages = 305–321 | date = 2015 | pmid = 26274026 | doi = 10.1146/annurev-micro-091014-104422 | quote = we review literature on trimethylamine (TMA), a microbiota-generated metabolite linked to atherosclerosis development.}}</ref><ref name="TMA diseases">{{cite journal | vauthors = Gaci N, Borrel G, Tottey W, O'Toole PW, Brugère JF | title = Archaea and the human gut: new beginning of an old story | journal = World J. Gastroenterol. | volume = 20 | issue = 43 | pages = 16062–16078 | date = November 2014 | pmid = 25473158 | pmc = 4239492 | doi = 10.3748/wjg.v20.i43.16062 | quote = 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. }}</ref> TMA is metabolized by the liver to [[trimethylamine N-oxide]] (TMAO); TMAO is being investigated as a possible pro[[atherogenic]] substance which may accelerate [[atherosclerosis]] in those eating foods with a high content of TMA precursors.<ref name="TMA diseases">{{cite journal | vauthors = Gaci N, Borrel G, Tottey W, O'Toole PW, Brugère JF | title = Archaea and the human gut: new beginning of an old story | journal = World J. Gastroenterol. | volume = 20 | issue = 43 | pages = 16062–16078 | date = November 2014 | pmid = 25473158 | pmc = 4239492 | doi = 10.3748/wjg.v20.i43.16062 | quote = 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. }}</ref> TMA also causes the odor of some human [[infection]]s, [[bad breath]], and [[bacterial vaginosis]].
Trimethylamine is a [[full agonist]] of human [[TAAR5]],<ref name="pmid23393561">{{cite journal |vauthors=Wallrabenstein I, Kuklan J, Weber L, Zborala S, Werner M, Altmüller J, Becker C, Schmidt A, Hatt H, Hummel T, Gisselmann G |title=Human trace amine-associated receptor TAAR5 can be activated by trimethylamine |journal=PLOS ONE |volume=8 |issue=2 |pages=e54950 |year=2013 |pmid=23393561 |pmc=3564852 |doi=10.1371/journal.pone.0054950 |bibcode=2013PLoSO...854950W |doi-access=free }}</ref><ref name="hTAAR5 ligands">{{cite journal | vauthors = Zhang J, Pacifico R, Cawley D, Feinstein P, Bozza T | title = Ultrasensitive detection of amines by a trace amine-associated receptor | journal = J. Neurosci. | volume = 33 | issue = 7 | pages = 3228–39 |date=February 2013 | pmid = 23407976 | pmc = 3711460 | doi = 10.1523/JNEUROSCI.4299-12.2013 | quote = 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).}}</ref><ref name="Microbial biosynthesis of bioactive compounds">{{cite journal | vauthors = Zhang LS, Davies SS | title = Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions | journal = Genome Med | volume = 8 | issue = 1 | pages = 46 | date = April 2016 | pmid = 27102537 | pmc = 4840492 | doi = 10.1186/s13073-016-0296-x }}<br />[https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4840492/table/Tab2/ Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease]<br />[https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4840492/figure/Fig1/ Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease]</ref> a [[trace amine-associated receptor]] that is expressed in the [[olfactory epithelium]] and functions as an [[olfactory receptor]] for [[tertiary amine]]s.<ref name="Microbial biosynthesis of bioactive compounds" /><ref name="TAAR 2015 review - olfactory TAARs">{{cite journal | vauthors = Liberles SD | title = Trace amine-associated receptors: ligands, neural circuits, and behaviors | journal = Curr. Opin. Neurobiol. | volume = 34 | pages = 1–7 | date = October 2015 | pmid = 25616211 | doi = 10.1016/j.conb.2015.01.001 | pmc = 4508243 }}</ref> One or more additional odorant receptors appear to be involved in trimethylamine olfaction in humans as well.<ref name="TAAR 2015 review - olfactory TAARs" />
==Production==
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== Toxicity ==
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]].<ref>{{cite journal|pmid=7023344|year=1981|last1=Wills|first1=M. R.|title=Biochemistry of renal failure|journal=Annals of Clinical and Laboratory Science|volume=11|issue=4|pages=292–9|last2=Savory|first2=J.}}</ref> In patients, trimethylamine caused stomach ache, vomiting, diarrhoea, lacrimation, greying of the skin and agitation.<ref>{{Cite journal|date=1929|title=Gifte und Vergiftungen. Vierte Ausgabe des Lehrbuches der Toxikologie. Von Prof. Louis Lewin. Mit 41 Figuren und einer farbigen Spektraltafel. Berlin 1929. Verlag von Georg Stilke. 1087 Seiten. Preis geh. 50,— Mark, geb. 55,— Mark|journal=Archiv der Pharmazie|volume=267|issue=4|pages=322–323|doi=10.1002/ardp.19292670410|s2cid=221459303|issn=0365-6233}}</ref> Apart from that, [[Reproductive toxicity|reproductive]]/[[developmental toxicity]] has been reported.<ref name=":0" />
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.<ref>{{Cite book|title=SCOEL/REC/179 trimethylamine recommendation from the Scientific Committee on Occupational Exposure Limits.|last=European Commission. Directorate-General for Employment, Social Affairs and Inclusion. Scientific Committee on Occupational Exposure Limits.|date=2017|publisher=Publications Office|oclc=1032584642}}</ref>
Some experimental studies suggested that TMA may be involved in etiology of [[Cardiovascular disease|cardiovascular diseases]].<ref>{{Cite journal|
==Applications==
Trimethylamine is used in the synthesis of [[choline]], [[tetramethylammonium hydroxide]], [[plant growth regulator]]s, [[herbicide]]s, strongly basic [[ion exchange resin|anion exchange resins]], [[dye]] leveling agents and a number of basic dyes.<ref name=Ullmann/><ref>{{cite book|title=Ashford's Dictionary of Industrial Chemicals|edition=3rd|year= 2011| page =9362|isbn=978-0-9522674-3-0|last1=Ashford|first1=Robert D.}}</ref> Gas sensors to test for fish freshness detect trimethylamine.
==Reactions==
Trimethylamine is a [[Lewis base]] that forms [[adducts]] with a variety of [[Lewis acids]].<ref>{{cite journal|author1=Cramer, R. E. |author2=Bopp, T. T. |year=1977|title= Graphical display of the enthalpies of adduct formation for Lewis acids and bases |journal= Journal of Chemical Education |volume=54|pages=
==Trimethylaminuria==
{{Main|Trimethylaminuria}}
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]].<ref name="Pearson">{{cite journal |
==See also==
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