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 =
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| 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]]
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[[fr:Triméthylamine]]
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[[ja:トリメチルアミン]]