Common NameTrimethylamine
DescriptionTrimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 degree centigrade and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid. Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath. It is also associated with taking large doses of choline. Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. Trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell. Trimethylamine in the urine is a biomarker for the consumption of legumes. It has also been found to be a product of various types of bacteria, such as Achromobacter, Acinetobacter, Actinobacteria, Aeromonas, Alcaligenes, Alteromonas, Anaerococcus, Bacillus, Bacteroides, Bacteroidetes, Burkholderia, Campylobacter, Citrobacter, Clostridium, Desulfitobacterium, Desulfovibrio, Desulfuromonas, Edwardsiella, Enterobacter, Enterococcus, Escherichia, Eubacterium, Firmicutes, Flavobacterium, Gammaproteobacteria, Haloanaerobacter, Klebsiella, Micrococcus, Mobiluncus, Olsenella, Photobacterium, Proteobacteria, Proteus, Providencia, Pseudomonas, Rhodopseudomonas, Ruminococcus, Salmonella, Sarcina, Serratia, Shewanella, Shigella, Sinorhizobium, Sporomusa, Staphylococcus, Stigmatella, Streptococcus, Vibrio and Yokenella (PMID:26687352 ; PMID:25108210 ; PMID:24909875 ; PMID:28506279 ; PMID:27190056 ). Trimethylamine is a marker for urinary tract infection brought on by E. coli. (PMID:25108210 ; PMID:24909875 ). It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ).
Structure
Molecular FormulaC3H9N
Average Mass59.11030
Monoisotopic Mass59.07350
IUPAC Nametrimethylamine
Traditional NameTrimethylamine
CAS Registry Number75-50-3
SMILESCN(C)C
InChI IdentifierInChI=1S/C3H9N/c1-4(2)3/h1-3H3
InChI KeyGETQZCLCWQTVFV-UHFFFAOYSA-N
CHEBI IDCHEBI:58389
HMDB IDHMDB0000906
MiMeDB IDMMDBc0000168
StateLiquid
Water Solubility6.54e+02 g/l
logP-0.14
logS1.04
pKa (Strongest Acidic)Not Available
pKa (Strongest Basic)9.57
Hydrogen Acceptor Count1
Hydrogen Donor Count0
Polar Surface Area3.24 Ų
Rotatable Bond Count0
Physiological Charge1
Formal Charge0
Refractivity19.99 m³·mol⁻¹
Polarizability7.64

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