Compound Summary

General Compound Information

trimethylamine

Description
Trimethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an methyl group. It has a role as a human xenobiotic metabolite and an Escherichia coli metabolite. It is a tertiary amine and a member of methylamines. It is a conjugate base of a trimethylammonium.
Synonyms
trimethylamine;  N,N-dimethylmethanamine;  75-50-3;  Methanamine, N,N-dimethyl-;  N-Trimethylamine;
FlavorDB ID
3113
PUBCHEM ID
Molecular Weight
59.11
Molecular Formula
C3H9N
Openeye Can Smiles
CN(C)C
IUPAC Inchikey
GETQZCLCWQTVFV-UHFFFAOYSA-N
Compound Classification
  • ClassyFire Ontology
Compound Quality
CATEGORY QUALITY THRESHOLD OCCURENCE REFERENCE
smell 4.400e+2 µg/kg blanched prawnfried prawn details
smell pungent,fishy,ammonia water details
smell pungent,fishy,ammonia 3.555e-3 µmol/L water details
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION AND USE: Trimethylamine (TMA) is a colorless gas. It is used in the manufacture of quaternary ammonium compounds, as an insect attractant, as a warning agent for natural gas, and as a corrosion inhibitor. It is also a synthetic flavor ingredient.
HUMAN STUDIES: Potential symptoms of overexposure to TMA are irritation of the eyes, skin, nose, throat, and respiratory system, as well as cough, dyspnea, delayed pulmonary edema, blurred vision, corneal necrosis, and skin burns. Direct contact with liquid may cause frostbite. Trimethylaminuria or "fish odor syndrome" described in human patients is due to excessive excretion into body fluids and breath of TMA derived from the enterobacterial metabolism of dietary precursors. Comparison of the effects of administration of antibiotics (metronidazole, amoxicillin, neomycin) on gut bacterial production of TMA from choline showed they all reduced TMA production to a limited extent, with neomycin being most effective.
ANIMAL STUDIES: Tests of single drops of aqueous solution applied to animal eyes have shown that 1% solution causes severe irritation, 5% causes hemorrhagic conjunctivitis, and 16.5% causes a severe reaction with conjunctival hemorrhages, corneal edema, and opacities, followed by some clearing but much vascularization. TMA is an emetic in dogs at an oral dose of 1000 mg/kg. At the same oral dose, TMA induced emesis and produced anorexia, paralysis, and death in pigs within 48 hours. In a repeated inhalation exposure study, groups of rats were exposed 6 hr/day, 5 days/week for 2 weeks at 0, 75, 250, or 750 ppm TMA vapor. After 10 exposures, histopathologic examination revealed concentration-dependent degenerative changes in the nasal olfactory and respiratory mucosa at all exposure levels. A similar degeneration of the tracheal mucosa was observed at 250 and 750 ppm. In mice, intraperitoneal injections (daily from day 1 to 17 of gestation) of TMA at 2.5 and 5 mmol/kg/day significantly decreased fetal body weight but not the placental weight or maternal body weight gain, however, 5 of 11 mice treated with 5 mmol/kg TMA died. TMA was tested in as many as 5 Salmonella typhimurium strains (TA 1535, TA 1537, TA 97, TA 98, and TA 100) in the presence and absence of metabolic activation. TMA was negative in these tests at doses of 0.010, 0.033, 0.10, 0.33 and 1.0 mg/plate. The highest ineffective dose tested in any S. typhimurium strain was 1.000 mg/plate.
ECOTOXICITY STUDIES: TMA caused inhibition to nitrifiers. Inhibition tests were conducted by using the oxygen utilization rate test with an enhanced nitrifier culture.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Food Additive Safety (OFAS)
TRIMETHYLAMINE is used for FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.
EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Trimethylamine
Receptors
Receptor information of this compound is not available!
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental GCMS view GCMS positive
Experimental LCMS view LCMS_Positive positive