Trimethylamine

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Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry.[1][2] At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact.[3] At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.

Physical and chemical properties

TMA is a colorless, hygroscopic, and flammable tertiary amine. It is a gas at room temperature but is usually sold as a 40% solution in water. It is also sold in pressurized gas cylinders.

TMA protonates to give the trimethylammonium cation. Trimethylamine is a good nucleophile, and this reactivity underpins most of its applications. Trimethylamine is a Lewis base that forms adducts with a variety of Lewis acids.[4]

Production

Industry and laboratory

Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:[1]

3 CH3OH + NH3 → (CH3)3N + 3 H2O

This reaction coproduces the other methylamines, dimethylamine (CH3)2NH and methylamine CH3NH2.

Trimethylammonium chloride has been prepared by a reaction of ammonium chloride and paraformaldehyde:[5]

9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2

Biosynthesis

Trimethylamine is produced by several routes in nature. Well studied are the degradation of choline and carnitine.[6]

Applications

Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, herbicides, strongly basic anion exchange resins, dye leveling agents and a number of basic dyes.[1][2] Gas sensors to test for fish freshness detect trimethylamine.

Toxicity

In humans, ingestion of certain plant and animal (e.g., red meat, egg yolk) food containing lecithin, choline, and L-carnitine provides certain gut microbiota with the substrate to synthesize TMA, which is then absorbed into the bloodstream.[7][8] High levels of trimethylamine in the body are associated with the development of trimethylaminuria, or fish odor syndrome, caused by a genetic defect in the enzyme which degrades TMA; or by taking large doses of supplements containing choline or L-carnitine.[7][8] TMA is metabolized by the liver to trimethylamine N-oxide (TMAO); TMAO is being investigated as a possible proatherogenic substance which may accelerate atherosclerosis in those eating foods with a high content of TMA precursors.[8] TMA also causes the odor of some human infections, bad breath, and bacterial vaginosis.

Trimethylamine is a full agonist of human TAAR5,[9][10][11] a trace amine-associated receptor that is expressed in the olfactory epithelium and functions as an olfactory receptor for tertiary amines.[11][12] One or more additional odorant receptors appear to be involved in trimethylamine olfaction in humans as well.[12]

Acute and chronic toxic effects of TMA were suggested in medical literature as early as the 19th century. TMA causes eye and skin irritation, and it is suggested to be a uremic toxin.[13] In patients, trimethylamine caused stomach ache, vomiting, diarrhoea, lacrimation, greying of the skin and agitation.[14] Apart from that, reproductive/developmental toxicity has been reported.[3] Some experimental studies suggested that TMA may be involved in etiology of cardiovascular diseases.[15][16]

Guidelines with exposure limit for workers are available e.g. the Recommendation from the Scientific Committee on Occupational Exposure Limits by the European Union Commission.[17]

Trimethylaminuria

Script error: No such module "Labelled list hatnote". Trimethylaminuria is an autosomal recessive genetic disorder involving a defect in the function or expression of flavin-containing monooxygenase 3 (FMO3) which results in poor trimethylamine metabolism. Individuals with trimethylaminuria develop a characteristic fish odor—the smell of trimethylamine—in their sweat, urine, and breath after the consumption of choline-rich foods. 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.[18][19]

In the history of psychoanalysis

The first dream of his own which Sigmund Freud tried to analyse in detail, when he was developing his theories about the interpretation of dreams, involved a patient of Freud's who had to have an injection of trimethylamine, and the chemical formula of the substance, written in bold letters on the bottle, jumping out at Freud.[20]

See also

References

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    Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
    Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
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  20. ↑ Sigmund Freud, Standard Ed., 4:116-119.

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External links

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