Trimethylamine

Trimethylamine, also known as NMe₃, N(CH₃)₃, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia-like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 °C and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid.

Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath.

Applications

Trimethylamine is used in the chemical synthesis of choline, tetramethyl ammonium hydroxide, plant growth regulators, strongly basic anion exchange resins, and dye leveling agents.

Trimethylaminuria

Trimethylaminuria is a genetic disorder were the body is unable to metabolize trimethylamine from food sources. Patients developed 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. Trimethylaminuria has also been observed for a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell.

See also

• Ammonia, NH₃
• Ammonium, NH₄⁺
• Methylamine
• Dimethylamine
• Triethylamine (TEA)

External links

• Molecule of the Month: Trimethylamine
• NIST Webbook data