Compound: TRIMETHYLAMINE N-OXIDE
SMILES: [O-][N+](C)(C)C
InChIKey: UYPYRKYUKCHHIB-UHFFFAOYSA-N
Synonyms: TRIMETHYLAMINE N-OXIDE, 1184-78-7, Trimethylamine oxide, N,N-dimethylmethanamine oxide, Triox, TMAO, Trimethyloxamine, N,N-Dimethylmethanamine N-oxide, Methanamine, N,N-dimethyl-, N-oxide, trimethylammonium oxide, (CH3)3NO, FLD0K1SJ1A, NSC-408426, FEMA NO. 4245, CHEBI:15724, RefChem:933449, 214-675-6, Trimethylamine N-oxide dihydrate, trimethylamine-N-oxide, TMANO, Trimethylamine, N-oxide, Trimethylaminoxid, TRIMETHYLAMINE N-OXIDE HYDROCHLORIDE, trimethylamineoxide, MFCD00002048, N(CH3)3O, Trimethylamine N-oxide anhydrous, N,N-dimethylmethanamine oxide (IUPAC), TMAe, EINECS 214-675-6, UNII-FLD0K1SJ1A, NSC 408426, AI3-60110, trimethylaminoxide, DTXSID8049678, TMA-oxide, Trimethlamine-N-oxide, 85408-49-7, trimethyl-oxido-ammonium, TRIMENTHLAMINE-N-O, bmse000426, Me3N(O), SCHEMBL119284, N,N,N-Trimethylamine N-oxide, orb1945027, orb3141429, Trimethylamine-N-oxide (TMAO), Trimethylamine, N-oxide (8CI), UYPYRKYUKCHHIB-UHFFFAOYSA-, MSK2588, N,N-Dimethyl-methanamine-N-oxide, TRIMETHYLAMINE N-OXIDE HCL, Me3N(+)O(-), Methanamine,N-dimethyl-, N-oxide, HMS6018N04, TRIMETHYLAMINE OXIDE [FHFI], TRIMETHYLAMINE N-OXIDE [MI], NSC408426, AKOS015917746, EBC-615860, FT15235, AS-62713, SY112165, DB-061286, HY-116084, CS-0063748, NS00021547, T1362, A11929, C01104, EN300-396337, InChI=1/C3H9NO/c1-4(2,3)5/h1-3H3, F511035, Q419802
Theoretical properties:
molecular_formula: C3H9NO
molecular_weight: 75.11 g/mol
exact_mass: 75.068413911 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 0
heavy_atom_count: 5
topological_polar_surface_area: 18.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 95 - 99 °C
solubility: 454 mg/mL
Descriptions:
pubchem: Trimethylamine N-oxide is a tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine. It has a role as a metabolite, an osmolyte and an Escherichia coli metabolite. It is functionally related to a trimethylamine. It is a conjugate base of a hydroxytrimethylaminium.
chebi: A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine.
wikipedia: 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.
TMAO is found in the tissues of marine crustaceans and marine fish, where it prevents water pressure from denaturing 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).
In animals, TMAO is a product of the oxidation of trimethylamine, a common metabolite of trimethyl quaternary ammonium compounds, like choline, trimethylglycine, and L-carnitine. High TMAO concentrations are associated with an increased risk of all-cause mortality and cardiovascular disease.