|Jmol-3D images||Image 1|
|Molar mass||59.11 g mol−1|
|Density||670 mg mL−1 (at 0 °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|
|Solubility in water||Miscible|
|Vapor pressure||91.74 kPa (at 21 °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|
|EU classification||F+ Xn|
|R-phrases||R12, R20, R37/38, R41|
|S-phrases||(S2), S16, S26, S29|
|Flash point||−7 °C (19 °F; 266 K)|
|LD50||500 mg kg−1 (oral, rat)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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 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.
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.
- 3 CH3OH + NH3 → (CH3)3N + 3 H2O
- 9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2↑
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 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 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.
- 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.; Coll. Vol. 1: 75
- Ashford's Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 9362. ISBN 978-0-9522674-3-0.
- Molecule of the Month: Trimethylamine
- NIST Webbook data
- CDC - NIOSH Pocket Guide to Chemical Hazards
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