Trimethylamine ( TMA) is an organic compound with the formula N(CH3)3. It is a Methylation derivative of ammonia. TMA is widely used in industry.
Physical and chemical properties
TMA is a colorless, hygroscopic, and flammable tertiary amine. It is a gas at room temperature but is usually sold as a 40% solution in water. It is also sold in pressurized .
TMA Protonation to give the trimethylammonium cation. Trimethylamine is a good nucleophile, and this reactivity underpins most of its applications. Trimethylamine is a Lewis base that forms adducts with a variety of Lewis acids.
Production
Industry and laboratory
Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:
- 3 CH3OH + NH3 → (CH3)3N + 3 H2O
This reaction coproduces the other methylamines, dimethylamine (CH3)2NH and methylamine CH3NH2.
Trimethylammonium chloride has been prepared by a reaction of ammonium chloride and paraformaldehyde:
- 9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2
Biosynthesis
Trimethylamine is produced by several routes in nature. Well studied are the degradation of choline and carnitine.
Applications
Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, , strongly basic anion exchange resins, dye leveling agents and a number of basic dyes.
Toxicity
In humans, ingestion of certain plant and animal (e.g., red meat, egg yolk) food containing lecithin, choline, and L-carnitine provides certain gut microbiota with the substrate to synthesize TMA, which is then absorbed into the bloodstream.
Trimethylamine is a full agonist of human TAAR5,
Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
Acute and chronic toxic effects of TMA were suggested in medical literature as early as the 19th century. TMA causes eye and skin irritation, and it is suggested to be a uremic toxin.
Guidelines with exposure limit for workers are available e.g. the Recommendation from the Scientific Committee on Occupational Exposure Limits by the European Union Commission.
Trimethylaminuria
Trimethylaminuria is an autosomal recessive genetic disorder involving a defect in the function or expression of flavin-containing monooxygenase 3 (FMO3) which results in poor trimethylamine metabolism. Individuals with trimethylaminuria develop a characteristic fish odor—the smell of trimethylamine—in their sweat, urine, and breath after the consumption of choline-rich foods. A condition similar to trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell, especially after eating food containing a high proportion of rapeseed.
In the history of psychoanalysis
The first dream of his own which Sigmund Freud tried to analyse in detail, when he was developing his theories about the interpretation of dreams, involved a patient of Freud's who had to have an injection of trimethylamine, and the chemical formula of the substance, written in bold letters on the bottle, jumping out at Freud.[Sigmund Freud, Standard Ed., 4:116-119.]
See also
External links
