Methyl carbamate (also called methylurethane, or urethylane) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

and the simplest ester of

carbamic acid Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula . It can be obtained by the reaction of ammonia and carbon dioxide at very low temperatures, which also yields ammoni ...

(H₂NCO₂H). It is a colourless solid. Methyl carbamate is prepared by the reaction of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

and

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

: :CO(NH₂)₂ + CH₃OH → CH₃OC(O)NH₂ + NH₃ It also forms in the reaction of

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

with

methyl chloroformate Methyl chloroformate is a chemical compound with the chemical formula . It is the methyl ester of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor. Preparation Methyl ...

dimethyl carbonate Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion ba ...

Safety and occurrence

Unlike its close relative

ethyl carbamate Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely use ...

it is not mutagenic in ''

Salmonella ''Salmonella'' is a genus of bacillus (shape), rod-shaped, (bacillus) Gram-negative bacteria of the family Enterobacteriaceae. The two known species of ''Salmonella'' are ''Salmonella enterica'' and ''Salmonella bongori''. ''S. enterica'' ...

'' (it tested negative in the

Ames test The Ames test is a widely employed method that uses bacteria to test whether a given chemical can cause mutations in the DNA of the test organism. More formally, it is a bioassay, biological assay to assess the mutagenic potential of chemical com ...

), but it is mutagenic in ''

Drosophila ''Drosophila'' (), from Ancient Greek δρόσος (''drósos''), meaning "dew", and φίλος (''phílos''), meaning "loving", is a genus of fly, belonging to the family Drosophilidae, whose members are often called "small fruit flies" or p ...

''. Experimental evidence does show that it is a carcinogen in

rat Rats are various medium-sized, long-tailed rodents. Species of rats are found throughout the order Rodentia, but stereotypical rats are found in the genus ''Rattus''. Other rat genera include '' Neotoma'' (pack rats), '' Bandicota'' (bandicoo ...

s, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per

Proposition 65 Proposition 65 (formally titled The Safe Drinking Water and Toxic Enforcement Act of 1986, and also referred to as Prop 65) is a California law passed by direct voter initiative in 1986 by a 63%–37% vote. Its goals are to protect drinking wate ...

Production, use, and exposure

The compound was detected in

wine Wine is an alcoholic drink made from Fermentation in winemaking, fermented fruit. Yeast in winemaking, Yeast consumes the sugar in the fruit and converts it to ethanol and carbon dioxide, releasing heat in the process. Wine is most often made f ...

s preserved with

dimethyl dicarbonate Dimethyl dicarbonate (DMDC) is a colorless liquid with a pungent odor at high concentration at room temperature. It is primarily used as a beverage preservative, processing aid, or sterilant ( INS No. 242) being highly active against typical beve ...

. Methyl carbamate is used primarily in the textile and polymer industries as a reactive intermediate. In the textile industry, it is used in the manufacture of dimethylol methyl carbamate-based resins that are applied on polyester cotton blend fabrics as durable-press finishes. The treated fabrics have good crease-angle retention, resist acid souring in commercial laundries, do not retain chlorine, and have flame-retardant properties. Methyl carbamate also is used in the manufacture of pharmaceuticals, insecticides, and urethane. N-Methyl carbamates are widely used as insecticides.National Pesticide Information Center at Oregon State University
/ref> They have

anticholinesterase Cholinesterase inhibitors (ChEIs), also known as anti-cholinesterase, are chemicals that prevent the breakdown of the neurotransmitter acetylcholine or butyrylcholine by cholinesterase. This increases the amount of the acetylcholine or butyryl ...

activity without a cumulative effect.

References

{{Reflist

External links

MSDS1987 NIH study of methyl carbamate's carcinogenicity
(PDF file) Methyl esters Carbamates

Safety and occurrence

Production, use, and exposure

See also

References

External links