FComEx: Trimethylamine oxide (PC000321)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:51 UTC

Update date

2017-01-19 02:36:19 UTC

FoodComEx ID

PC000321

FoodDB Record

FDB010413

Chemical Information

Name

Trimethylamine oxide

Description

Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counter-act the effects of increased concentrations of urea (due to kidney failure) and can be used as a biomarker for kidney problems. Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor.; Trimethylamine N-oxide, also known by several other names and acronyms, is the organic compound with the formula (CH3)3NO. This colorless solid is usually encountered as the dihydrate. It is an oxidation product of trimethylamine and a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks and rays, molluscs, and crustaceans. Along with free amino acids, it reduces the 3% salinity of seawater to about 1% of dissolved solids inside cells. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.; Trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3),, causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor. Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish.

CAS Number

1184-78-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(CH3)3NO	biospider
Me3N(+)O(-)	ChEBI
Me3N(O)	ChEBI
Methanamine, n,n-dimethyl-, n-oxide	biospider
N,n-dimethylmethanamine n-oxide	biospider
N,n-dimethylmethanamine oxide	biospider
N,n-dimethylmethanamine oxide (iupac)	biospider
N(CH3)3O	biospider
Tma-oxide	biospider
Tmano	biospider
TMAO	biospider
Trimenthlamine-n-o	biospider
Trimethylamine n-oxide	biospider
Trimethylamine n-oxide dihydrate	biospider
Trimethylamine-n-oxide	biospider
Trimethylamine, n-oxide	biospider
Trimethylamine, N-oxide (8CI)	biospider
Trimethylaminoxid	biospider
Trimethylammonium oxide	biospider
Trimethyloxamine	biospider
Triox	biospider

Chemical Formula

C3H9NO

IUPAC name

N,N-dimethylmethanamine oxide

InChI Identifier

InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3

InChI Key

UYPYRKYUKCHHIB-UHFFFAOYSA-N

Isomeric SMILES

C[N+](C)(C)[O-]

Average Molecular Weight

75.1097

Monoisotopic Molecular Weight

75.068413915

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trialkyl amine oxides. These are hydrocarbyl derivatives of the aminoxide anion, with the general formula R3N+[O-] or R3N=O, where R is an alkyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Aminoxides

Direct Parent

Trialkyl amine oxides

Alternative Parents

Substituents