Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It 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 is a nitrogenous base and can be readily protonated to give the 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. TMA is widely used in industry: it 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.[5][6] At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact.[7] At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.
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.[8][9] 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.[8][9] 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.[9] TMA also causes the odor of some human infections, bad breath, and bacterial vaginosis.
Trimethylamine is a full agonist of human TAAR5,[10][11][12] a trace amine-associated receptor that is expressed in the olfactory epithelium and functions as an olfactory receptor for tertiary amines.[12][13] One or more additional odorant receptors appear to be involved in trimethylamine olfaction in humans as well.[13]
| Names | |
|---|---|
| Preferred IUPAC name N,N-Dimethylmethanamine | |
| Other names (Trimethyl)amine (The name trimethylamine is deprecated.)[2] |
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]
Some experimental studies suggested that TMA may be involved in etiology of cardiovascular diseases.[18][19]
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 Redchicken that produces eggs with a fishy smell, especially after eating food containing a high proportion of rapeseed.[22][23]
- Ammonia, NH3
- Ammonium, NH4+
- Methylamine, (CH3)NH2
- Triethylamine (TEA)
| Related compounds | |
|---|---|
Related amines | |
Related compounds | |
| TAAR1 |
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| TAAR2 |
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| TAAR5 |
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https://en.wikipedia.org/wiki/Trimethylamine
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