Trimethylamine N-oxide

Trimethylamine N-oxide (TMAO) is an organic compound with the formula (CH3)3NO. It is in the class of amine oxides. Although the anhydrous compound is known, trimethylamine N-oxide is usually encountered as the dihydrate. Both the anhydrous and hydrated materials are white, water-soluble solids.

Trimethylamine N-oxide
Names
Preferred IUPAC name
N,N-Dimethylmethanamine N-oxide
Other names
Trimethylamine oxide, TMAO, TMANO
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.341
KEGG
UNII
  • 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
  • C[N+](C)(C)[O-]
Properties
C3H9NO
Molar mass 75.11
Appearance colorless solid
Melting point 220 to 222 °C (428 to 432 °F; 493 to 495 K) (dihydrate: 96 °C)
good
5.4 D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

TMAO is found in the tissues of marine crustaceans and marine fish, where it prevents water pressure from distorting proteins and thus killing the animal. The concentration of TMAO increases with the depth at which the animal lives; TMAO is found in high concentrations in the deepest-living described fish species, Pseudoliparis swirei, which was found in the Mariana Trench, at a recorded depth of 8,076 m (26,496 ft).

TMAO is a product of the oxidation of trimethylamine, a common metabolite of choline in animals.

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