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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. 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 employing a catalyst:[2]
- 3CH3OH + 2NH3 -> (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:
- 3(CH2=O)3 + 2NH4Cl -> 2CH3)3N *HCl
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
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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
References
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