Trimethylamine oxide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Trimethylamine oxide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Trimethylamine oxide?

The molecule Trimethylamine oxide presents a molecular formula of C3H9NO and its IUPAC name is N,N-dimethylmethanamine oxide.

Trimethylamine oxide (TMAO) is a molecule that is produced in the gut when certain foods are digested. TMAO has been linked to an increased risk of heart disease and stroke, and recent studies have shown that it may also be involved in the development of Alzheimer's disease..

TMAO is produced by gut bacteria when they break down choline, a nutrient found in eggs, meat, and dairy products. Choline is also found in some plant-based foods, but it is not broken down by gut bacteria..

The body converts TMAO into trimethylamine (TMA), which is then metabolized by the liver. TMA is a foul-smelling compound that is released in the sweat, urine, and breath..

High levels of TMAO have been linked to an increased risk of heart disease and stroke. In one study, people with the highest levels of TMAO were more than twice as likely to have a heart attack or stroke as those with the lowest levels..

Recent studies have also shown that TMAO may be involved in the development of Alzheimer's disease. In one study, people with the highest levels of TMAO were more than three times as likely to develop Alzheimer's disease as those with the lowest levels..

The exact role of TMAO in the development of these diseases is not yet clear, but it is thought that TMAO may promote the buildup of plaques in the arteries and brain..

Reducing the amount of TMAO in the body may help to reduce the risk of these diseases. This can be done by avoiding foods that contain choline and by taking probiotics or antibiotics that reduce the amount of TMAO-producing gut bacteria..

3D structure

Cartesian coordinates

Geometry of Trimethylamine oxide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Trimethylamine oxide UYPYRKYUKCHHIB-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Trimethylamine oxide

 

Molecule descriptors

 
IUPAC nameN,N-dimethylmethanamine oxide
InChI codeInChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
InChI KeyUYPYRKYUKCHHIB-UHFFFAOYSA-N
SMILESC[N+](C)(C)[O-]

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (CH3)3NO
  • 1184-78-7
  • 85408-49-7
  • A803941
  • AI3-60110
  • AS-62713
  • Amines, C12-16-alkyldimethyl, N-oxides
  • C01104
  • CS-0063748
  • DB-061286
  • FEMA NO. 4245
  • FLD0K1SJ1A
  • FT-0675602
  • FT-0697390
  • HY-116084
  • J-003759
  • MFCD00002048
  • Me3N(+)O(-)
  • Me3N(O)
  • Methanamine, N,N-dimethyl-, N-oxide
  • Methanamine,N-dimethyl-, N-oxide
  • N(CH3)3O
  • N,N-Dimethyl-methanamine-N-oxide
  • N,N-Dimethylmethanamine N-oxide
  • N,N-dimethylmethanamine oxide
  • N,N-dimethylmethanamine oxide (IUPAC)
  • NSC 408426
  • NSC-408426
  • NSC408426
  • Q419802
  • T0466
  • T1362
  • TMA-oxide
  • TMANO
  • TMAO
  • TMAe
  • TRIMENTHLAMINE-N-O
  • TRIMETHYLAMINE N-OXIDE
  • TRIMETHYLAMINE N-OXIDE HCL
  • TRIMETHYLAMINE N-OXIDE HYDROCHLORIDE
  • Trimethlamine-N-oxide
  • Trimethylamine N-oxide anhydrous
  • Trimethylamine oxide
  • Trimethylamine, N-oxide
  • Trimethylamine, N-oxide (8CI)
  • Trimethylaminoxid
  • Trimethyloxamine
  • Triox
  • UYPYRKYUKCHHIB-UHFFFAOYSA-
  • bmse000426
  • trimethyl amine oxide
  • trimethyl-oxido-ammonium
  • trimethylamine-N-oxide
  • trimethylamineoxide
  • trimethylaminoxide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC895494
  • UNII-FLD0K1SJ1A
  • AKOS015917746
  • DTXSID8049678
  • DTXSID001030179
  • CHEBI:15724
  • EINECS 214-675-6

Physico-Chemical properties

IUPAC nameN,N-dimethylmethanamine oxide
Molecular formulaC3H9NO
Molecular weight75.1097
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity22.80
LogP0.2
Topological polar surface area29.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.