(organic chemistry) (CH3)3N A colorless, liquefied gas with a fishy odor and a boiling point of -4°C; soluble in water, ether, and alcohol; used as a warning agent for natural gas, a flotation agent, and insect attractant. Abbreviated TMA.
Trimethylamine
| Sci-Tech Dictionary: trimethylamine |
(trī¦meth·ə·lə¦mēn)
| 5min Related Video: Trimethylamine |
| Medical Dictionary: tri·meth·yl·a·mine |
(trī-mĕth'ə-lə-mēn', -lăm'ēn, -mə-thĭl'ə-mēn')
n.
n.
A degradation product of nitrogenous plant and animal substances.
| Veterinary Dictionary: trimethylamine |
A smelly substance that taints milk. Formed in sugar beet residues by the fermentation of betaine.
| Wikipedia: Trimethylamine |
| Trimethylamine[1] | |
|---|---|
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|
 |
 |
| IUPAC name |
Trimethylamine
|
| Other names | N,N-Dimethylmethanamine |
| Identifiers | |
| Abbreviations | TMA, NMe3 |
| CAS number | 75-50-3  |
| PubChem | 1146 |
| EC number | 200-875-0 |
| RTECS number | 1.1.78 – 31.1.87 |
| SMILES |
CN(C)C
|
| InChI |
1/C3H8N/c1-4(2)3/h1H2,2-3H3
|
| ChemSpider ID | 1114 |
| Properties | |
| Molecular formula | C3H9N |
| Molar mass | 59.11 g/mol |
| Appearance | Colourless gas |
| Density | 0.67 g/mL (0 °C) |
| Melting point |
-117.08 °C, 156 K, -179 °F |
| Boiling point |
2.87 °C, 276 K, 37 °F |
| Solubility in water | Miscible |
| Basicity (pKb) | 4.13 |
| Hazards | |
| R-phrases | R12 R20/22 R34 |
| S-phrases | (S1/2) S3 S16 S26 S29 S36/37/39 S45 |
| NFPA 704 |
 4
2
0
|
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Trimethylamine 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 gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in 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 infections, 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. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.
Contents |
Production
Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:[2]
- 3 CH3OH + NH3 → (CH3)3N + 3 H2O
This reaction coproduces the other methylamines, (CH3)2NH and CH3NH2.
Trimethylamine has also been prepared via a reaction of ammonium chloride and paraformaldehyde,[3] according to the following equation:
- 9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2↑
Applications
Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, strongly basic anion exchange resins, and dye leveling agents.[2] Gas sensors to test for fish freshness detect trimethylamine.
Trimethylaminuria
Main article: 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, NH3
- Ammonium, NH4+
- Methylamine
- Dimethylamine
- Triethylamine (TEA)
References
- ^ Merck Index, 11th Edition, 9625.
- ^ a b 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
- ^ Roger Adams, B. K. Brown, "Trimethylamine", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0531; Coll. Vol. 1: 75
External links
This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)
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 | Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms. Copyright © 2003, 1994, 1989, 1984, 1978, 1976, 1974 by McGraw-Hill Companies, Inc. All rights reserved. Read more |
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| Medical Dictionary. The American Heritage® Stedman's Medical Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Company. Read more |
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| Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved. Read more |
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| Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Trimethylamine". Read more |
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Mentioned in
- triethylamine
- tertiary amine (organic chemistry)
- amines
- amine salts
