Trimethylamine 1620404 224260245 2008-07-08T01:19:42Z Smokefoot 698909 Info from Ullmann's, indicate the real prep {{chembox new | Reference = <ref>''Merck Index''<link rel="stylesheet" type="text/css" href="http://en.wikipedia.org/w/index.php?title=User:Lupin/navpop.css&action=raw&ctype=text/css&dontcountme=s">, 11th Edition, '''9625'''.</ref> | ImageFile = Trimethylamine_chemical_structure.png | ImageSize = 120px | ImageFileL1 = Trimethylamine-3D-balls.png | ImageSizeL1 = | ImageFileR1 = Trimethylamine-3D-vdW.png | ImageSizeR1 = | IUPACName = Trimethylamine | OtherNames = N,N-Dimethylmethanamine | Section1 = {{Chembox Identifiers | Abbreviations = TMA, NMe<sub>3</sub> | CASNo = 75-50-3 | EINECS = 200-875-0 | PubChem = 1146 | SMILES = CN(C)C | InChI = 1/C3H8N/c1-4(2)3/h1H2,2-3H3 | RTECS = 1.1.78 – 31.1.87 | MeSHName = | ChEBI = | KEGG = | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental =}} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>H<sub>9</sub>N | MolarMass = 59.11 g/mol | Appearance = Colourless gas | Density = 0.67 g/mL (0 °C) | MeltingPtC = -117.08 | Melting_notes = | BoilingPtC = 2.87 | Boiling_notes = | Solubility = Miscible | SolubleOther = | Solvent = | pKa = | pKb = 4.13}} | Section7 = {{Chembox Hazards | EUClass = | EUIndex = | MainHazards = | NFPA-H = 2 | NFPA-F = 4 | NFPA-R = 0 | NFPA-O = | RPhrases = {{R12}} {{R20/22}} {{R34}} | SPhrases = {{S1/2}} {{S3}} {{S16}} {{S26}} {{S29}} {{S36/37/39}} {{S45}} | RSPhrases = | FlashPt = | Autoignition = | ExploLimits = | PEL = }} }} '''Trimethylamine''' is an [[organic compound]] with the formula N(CH<sub>3</sub>)<sub>3</sub>. This colorless, [[hygroscopic]], and flammable [[tertiary amine]] has a strong "fishy" [[odor]] in low [[concentration]]s and an [[ammonia]]-like odor at higher concentrations. It is a gas at room temperature but is usually sold in pressurized [[gas cylinder]]s or as a 40% [[solution]] in [[Water (molecule)|water]]. Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the odor often associated with fouling [[fish]], some [[infection]]s, and [[bad breath]]. It is also associated with taking large doses of [[choline]] and [[carnitine]]. Trimethylamine is a [[nitrogenous base]] and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from [[hydrochloric acid]]. It is also a good [[nucleophile]], and this reaction is the basis of most of its applications. == Production == Trimethylamine is prepared by the reaction of [[ammonia]] and [[methanol]]:<ref name=Ullmann>A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. {{DOI|10.1002/14356007.a16 535}}</ref> :3CH<sub>3</sub>OH + 2NH<sub>3</sub> -> CH<sub>3</sub>)<sub>3</sub>N + 3 H<sub>2</sub>O This reaction coproduces the other methylamines, CH<sub>3</sub>)<sub>2</sub>NH and CH<sub>3</sub>NH<sub>2</sub>. Trimethylamine has also been prepared via a reaction of [[ammonium chloride]] and [[paraformaldehyde]],<ref>{{OrgSynth | author = [[Roger Adams]], B. K. Brown | title = Trimethylamine| collvol = 1 | collvolpages = 75 | prep = CV1P0531}}</ref> according to the following equation: :3(CH<sub>2</sub>=O)<sub>3</sub> + 2NH<sub>4</sub>Cl -> 2CH<sub>3</sub>)<sub>3</sub>N *HCl == Applications == Trimethylamine is used in the synthesis of [[choline]], [[tetramethylammonium hydroxide]], [[plant growth regulator]]s, strongly basic [[ion exchange resin|anion exchange resins]], and [[dye]] leveling agents.<ref name=Ullmann/> Gas sensors to test for fish freshness detect trimethylamine. == Trimethylaminuria == {{main|Trimethylaminuria}} 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. A trimethylaminuria-like condition 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]]. == See also == * [[Ammonia]], NH<sub>3</sub> * [[Ammonium]], NH<sub>4</sub><sup>+</sup> * [[Methylamine]] * [[Dimethylamine]] * [[Triethylamine]] (TEA) ==References== {{Reflist}} == External links == * [http://www.chm.bris.ac.uk/motm/trimethylamine/tmah.htm Molecule of the Month: Trimethylamine] * [http://webbook.nist.gov/cgi/cbook.cgi?Name=trimethylamine&Units=SI NIST Webbook data] [[Category:flavors]] [[Category:Amines]] [[de:Trimethylamin]] [[fr:Triméthylamine]] [[nl:Trimethylamine]] [[ja:トリメチルアミン]]