Record Information
Version1.0
Creation date2010-04-08 22:09:07 UTC
Update date2017-10-04 22:27:58 UTC
Primary IDFDB010413
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTrimethylamine oxide
DescriptionTrimethylamine 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 Number1184-78-7
Structure
Thumb
Synonyms
SynonymSource
(CH3)3NOChEBI
Me3n(+)O(-)ChEBI
Me3n(O)ChEBI
N(CH3)3OChEBI
TMAOChEBI
Trimethylamine oxideChEBI
TrimethylaminoxidChEBI
TrimethyloxamineChEBI
N,N-Dimethylmethanamine N-oxideHMDB
TMA-oxideHMDB
Trimethylamine-N-oxideHMDB
TrioxHMDB
Trimethylammonium oxideHMDB
Me3N(+)O(-)ChEBI
Me3N(O)ChEBI
Methanamine, n,n-dimethyl-, n-oxidebiospider
N,n-dimethylmethanamine n-oxidebiospider
N,n-dimethylmethanamine oxidebiospider
N,n-dimethylmethanamine oxide (iupac)biospider
Tma-oxidebiospider
Tmanobiospider
Trimenthlamine-n-obiospider
Trimethylamine n-oxidebiospider
Trimethylamine n-oxide dihydratebiospider
Trimethylamine-n-oxidebiospider
Trimethylamine, n-oxidebiospider
Trimethylamine, N-oxide (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility57.8 g/LALOGPS
logP-2ALOGPS
logP-0.93ChemAxon
logS-0.11ALOGPS
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.03 m³·mol⁻¹ChemAxon
Polarizability8.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H9NO
IUPAC nameN,N-dimethylmethanamine oxide
InChI IdentifierInChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
InChI KeyUYPYRKYUKCHHIB-UHFFFAOYSA-N
Isomeric SMILESC[N+](C)(C)[O-]
Average Molecular Weight75.1097
Monoisotopic Molecular Weight75.068413915
Classification
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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAminoxides
Direct ParentTrialkyl amine oxides
Alternative Parents
Substituents
  • Trialkyl amine oxide
  • Trisubstituted n-oxide
  • N-oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point95-99 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKa4.65
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-9000000000-426384c1c05ab5b584beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-056r-9000000000-9ba99fcfab36000c7757View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-77dcb5a2685e3154e9f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-dabc3f78669637484204View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-9000000000-0e637352d88abe7c2b0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-9000000000-d155aab0cf63bd6365caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-54c4798b9d38df37e8a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-7b4ea1bc9a14eef87f35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052f-9000000000-1e5a0675e8b58686f975View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-056r-9000000000-aeb64eb28a53521764cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-0e637352d88abe7c2b0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-d155aab0cf63bd6365caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-54c4798b9d38df37e8a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-7b4ea1bc9a14eef87f35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052f-9000000000-7f27d29305df82f75dfeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-9000000000-72bdd3a0798c28024038View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-ff78646c3e3f75afce16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-ed1a5c9cf14802f3a117View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-388e7087787fdbab7a18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-6298f48fa1844aa5f438View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-9ca491949ce95689c50cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-89485046f830076c9234View in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-28a96c1111fa94368c76View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID1113
ChEMBL IDNot Available
KEGG Compound IDC01104
Pubchem Compound ID1145
Pubchem Substance IDNot Available
ChEBI ID15724
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00925
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID3738
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDTMO
Flavornet IDNot Available
GoodScent IDrw1293651
SuperScent IDNot Available
Wikipedia IDTrimethylamine oxide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference