Trimethylamine

Trimethylamine (TMA) 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. TMA is a nitrogenous base and can be readily protonated to give trimethylammonium cations. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. TMA is a product of decomposition of plants and animals. In humans, it is synthesized exclusively by gut microbiota from dietary nutrients such as choline and carnitine.

Production and synthesis

TMA is derived from choline through the action of certain bacteria such as Desulfovibrio desulfuricans. It is also formed from trimethylamine N-oxide (TMAO) through the action of the enzyme flavin-containing monooxygenase 3 (FMO3). In humans, TMA is converted in the liver to TMAO through the action of FMO3.

Uses

TMA is used in the synthesis of quaternary ammonium compounds such as choline chloride, which is used as a feed additive. It is also used in the production of certain ion exchange resins and surfactants.

Health effects

High levels of TMA in the body can lead to a condition known as trimethylaminuria or "fish odor syndrome". This condition is characterized by a strong fishy odor in the breath, sweat, and urine of affected individuals. It is caused by mutations in the FMO3 gene, which result in decreased or absent activity of the FMO3 enzyme and thus an inability to convert TMA to TMAO.

See also

• Choline
• Carnitine
• Trimethylamine N-oxide
• Trimethylaminuria
• Flavin-containing monooxygenase 3

References

Trimethylamine Resources
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