Trimethylamine N-oxide

Trimethylamine N-oxide

Names
IUPAC name trimethylamine oxide
Preferred IUPAC name N,N-dimethylmethanamine oxide
Other names trimethylamine oxide, TMAO, TMANO
Identifiers
CAS Number	1184-78-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15724 Y
ChemSpider	1113 Y
ECHA InfoCard	100.013.341
KEGG	C01104 Y
PubChem CID	1145
UNII	FLD0K1SJ1A Y
InChI InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3 Y Key: UYPYRKYUKCHHIB-UHFFFAOYSA-N Y InChI=1/C3H9NO/c1-4(2,3)5/h1-3H3 Key: UYPYRKYUKCHHIB-UHFFFAOYAU
SMILES C[N+](C)(C)[O-]
Properties
Chemical formula	C3H9NO
Molar mass	75.11
Appearance	colorless solid
Melting point	220 to 222 °C (428 to 432 °F; 493 to 495 K) (hydrate: 96 °C)
Solubility in water	good
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Trimethylamine N-oxide (TMAO) is the organic compound in the class of amine oxides with the formula (CH₃)₃NO. This colorless solid is usually encountered as the dihydrate. It is a product of the oxidation of trimethylamine, a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks, rays, molluscs, and crustaceans. It is a protein stabilizer that may serve to counteract urea, the major osmolyte of sharks, skates and rays. It is also higher in deep-sea fishes and crustaceans, where it may counteract the protein-destabilizing effects of pressure. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.

TMAO can be synthesized from trimethylamine by treatment with hydrogen peroxide:

TMAO is biosynthesized from trimethylamine, which is derived from choline.

Trimethylaminuria is a rare defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3). Those suffering from trimethylaminuria are unable to convert choline-derived trimethylamine into trimethylamine oxide. Trimethylamine then accumulates and is released in the person's sweat, urine, and breath, giving off a strong fishy odor.

Trimethylamine oxide is used in protein folding experiments to counteract the unfolding effects of urea.

In the organometallic chemistry reaction of nucleophilic abstraction, Me₃NO is employed as a decarbonylation agent according to the following stoichiometry: