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Methylamine, also known as methanamine, is an organic compound with a chemical formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.
Methylamine is sold as a solution in methanol, ethanol, tetrahydrofuran, or water, or as the anhydrous gas in pressurized metal containers. Industrially, methylamine is transported in its anhydrous form in pressurized railcars and tank trailers. It has a strong odor similar to rotten fish. Methylamine is used as a building block for the synthesis of numerous other commercially available compounds.
/ref> and published an article in 1921.
It is now prepared commercially by the reaction of ammonia with methanol in the presence of an aluminosilicate catalyst. Dimethylamine and trimethylamine are co-produced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favored by the reaction kinetics is trimethylamine.
In the laboratory, methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride.
Another method entails reducing nitromethane with zinc and hydrochloric acid.
Another method of methylamine production is spontaneous decarboxylation of glycine with a strong base in water.
Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ephedrine and theophylline, the pesticides carbofuran, carbaryl, and metham sodium, and the solvents N-methylformamide and N-methylpyrrolidone. The preparation of some and photographic developers require methylamine as a building block.
Additionally, methylamine is produced during PADI4-dependent arginine demethylation.
The Occupational Safety and Health Administration (OSHA) and National Institute for Occupational Safety and Health (NIOSH) have set occupational exposure limits at 10 ppm or 12 mg/m3 over an eight-hour time-weighted average. CDC - NIOSH Pocket Guide to Chemical Hazards
Biological chemistry
Methylamine arises as a result of putrefaction and is a substrate for methanogenesis.
Safety
The LD50 (mouse, s.c.) is 2.5 g/kg. The Merck Index, 10th Ed. (1983), p.864, Rahway: Merck & Co.
Regulation
In the United States, methylamine is controlled as a List 1 drug precursor chemical by the Drug Enforcement Administration Title 21 Code of Federal Regulations due to its use in the illicit production of methamphetamine.
In popular culture
Fictional characters Walter White and Jesse Pinkman use Aqueous solution methylamine as part of a process to synthesize methamphetamine in the AMC series Breaking Bad.
See also
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