Trimethylamine

Trimethylamine (N(CH₃)₃) is a volatile organic compound with a strong fishy odor. It forms during the breakdown of choline and other compounds and occurs in biological systems and industrial processes.

Choline: Choline is an essential nutrient and precursor to phospholipids and the neurotransmitter acetylcholine. Gut microbes can convert choline into trimethylamine.
Trimethylaminuria: Trimethylaminuria is a metabolic disorder in which trimethylamine accumulates and causes a fish-like body odor. It is the clearest human condition directly associated with excess trimethylamine.
Amines: Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with carbon-containing groups. Trimethylamine is a tertiary amine with three methyl groups attached to nitrogen.
Betaine: Betaine is a trimethylated amino-acid derivative that functions as an osmolyte and methyl-group donor. Gut microbes can produce trimethylamine from betaine.
Trimethylamine N-oxide: Trimethylamine N-oxide is an odorless compound found in marine organisms and formed by oxidation of trimethylamine. The liver converts absorbed trimethylamine into this less volatile product.
Headspace gas chromatography: Headspace gas chromatography separates volatile compounds sampled from the gas above a liquid or solid. Its volatility makes trimethylamine suitable for headspace analysis.
Tertiary amine: A tertiary amine has a nitrogen atom bonded to three carbon-containing groups and no N–H bond. Trimethylamine is the simplest amine with three identical methyl substituents.
Dimethylamine: Dimethylamine is a secondary amine with formula (CH₃)₂NH and two methyl groups attached to nitrogen. It is a related volatile amine with one fewer methyl group than trimethylamine.
FMO3: FMO3 is a liver enzyme that oxidizes trimethylamine and several other nitrogen-containing compounds. Reduced FMO3 activity allows trimethylamine to accumulate in the body.
Fish spoilage: Fish spoilage is the deterioration of fish through microbial growth and chemical changes after capture. Microbial production of trimethylamine contributes to the odor of spoiled fish.

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