Trimethylamine N-oxide

Description

Trimethylamine N-oxide (TMAO) is a metabolite of choline, phosphatidylcholine, and L-carnitine . It is formed by gut microbiota-mediated metabolism of choline, phosphatidylcholine, and L-carnitine to TMA followed by oxidation of TMA by flavin-containing monooxygenase 3 (FMO3) in the liver. Dietary administration of TMAO (0.12% w/w) increases renal tubulointerstitial fibrosis, collagen deposition, and Smad3 phosphorylation in mice and increases aortic lesion area in atherosclerosis-prone ApoE^-/- mice. Plasma levels of TMAO are elevated in patients with chronic kidney disease and decreased in patients with active, compared with inactive, ulcerative colitis. Elevated plasma levels of TMAO are associated with increased risk of cardiovascular disease.

Chemical Properties

Colorless to yellow solid; odorless.

Chemical Properties

White crystalline powder

Uses

Trimethylamine?N-oxide can be used:

• As a demetallation?and decarbonylation?reagent for organometallic compounds.
• To prepare azomethine ylide by reaction with lithium di-isopropylamide. This, in turn, may be reacted with simple alkenes to obtain corresponding pyrrolidines.
• To mediate the conversion of thiols to disulfides.

Definition

ChEBI: An N-oxide derived from triethylamine.

General Description

Trimethylamine?N-oxide is an organic compound that belongs to the class of amine oxides. It is generally found in the tissues of marine organisms, wherein it helps protect them from harsh conditions like salinity, hydrostatic pressure, temperature, and high urea.

Flammability and Explosibility

Not classified