Methyl carbamate
Encyclopedia
Methyl carbamate is an organic compound
and the simplest ester of the hypothetical carbamic acid
(NH2COOH). Its sum formula is C2H5NO2.
Methyl carbamate is formed by the reaction of ammonia
with methyl chloroformate
or methyl carbonate. According to US patent
number 2834799 urea
can be reacted with methanol
to form it using boron trifluoride
as a reagent. Unlike its close relative ethyl carbamate
it is not mutagenic in salmonella
(it tested negative in the Ames test
), but it is mutagenic in Drosophila
. Experimental evidence does show that it is a carcinogen in rat
, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65
.
The compound was detected in wine
s preserved with dimethyl dicarbonate
.
Methyl carbamate is used by the textile industry to manufacture resins to be applied on polyester/cotton blend fabrics as durable-press finishes.
N-Methyl carbamates are widely used as insecticides.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
and the simplest ester of the hypothetical carbamic acid
Carbamic acid
Carbamic acid is a compound that is unstable under normal circumstances. It is technically the simplest amino acid, though its instability allows glycine to assume this title. Its importance is due more to its relevance in identifying the names of larger compounds...
(NH2COOH). Its sum formula is C2H5NO2.
Methyl carbamate is formed by the reaction of ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
with methyl chloroformate
Methyl chloroformate
Methyl chloroformate is the methyl ester of chloroformic acid. It is also known as methyl chlorocarbonate, and is an oily liquid with a colour that is anywhere from yellow to colorless. It is also known for its pungent odour...
or methyl carbonate. According to US patent
Patent
A patent is a form of intellectual property. It consists of a set of exclusive rights granted by a sovereign state to an inventor or their assignee for a limited period of time in exchange for the public disclosure of an invention....
number 2834799 urea
Urea
Urea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....
can be reacted with methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
to form it using boron trifluoride
Boron trifluoride
Boron trifluoride is the chemical compound with the formula BF3. This pungent colourless toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds.-Structure and bonding:...
as a reagent. Unlike its close relative ethyl carbamate
Ethyl carbamate
Ethyl carbamate is a chemical compound with the molecular formula C3H7NO2 first prepared in the nineteenth century. Structurally, it is an ester of carbamic acid...
it is not mutagenic in salmonella
Salmonella
Salmonella is a genus of rod-shaped, Gram-negative, non-spore-forming, predominantly motile enterobacteria with diameters around 0.7 to 1.5 µm, lengths from 2 to 5 µm, and flagella which grade in all directions . They are chemoorganotrophs, obtaining their energy from oxidation and reduction...
(it tested negative in the Ames test
Ames test
The Ames test is a biological assay to assess the mutagenic potential of chemical compounds. A positive test indicates that the chemical is mutagenic and therefore may act as a carcinogen, since cancer is often linked to mutation. However, a number of false-positives and false-negatives are known...
), but it is mutagenic in Drosophila
Drosophila
Drosophila is a genus of small flies, belonging to the family Drosophilidae, whose members are often called "fruit flies" or more appropriately pomace flies, vinegar flies, or wine flies, a reference to the characteristic of many species to linger around overripe or rotting fruit...
. Experimental evidence does show that it is a carcinogen in rat
Rat
Rats are various medium-sized, long-tailed rodents of the superfamily Muroidea. "True rats" are members of the genus Rattus, the most important of which to humans are the black rat, Rattus rattus, and the brown rat, Rattus norvegicus...
, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65
California Proposition 65 (1986)
Proposition 65 is a California law passed by direct voter initiative in 1986 by a 63%-37% margin...
.
The compound was detected in wine
Wine
Wine is an alcoholic beverage, made of fermented fruit juice, usually from grapes. The natural chemical balance of grapes lets them ferment without the addition of sugars, acids, enzymes, or other nutrients. Grape wine is produced by fermenting crushed grapes using various types of yeast. Yeast...
s preserved with dimethyl dicarbonate
Dimethyl dicarbonate
Dimethyl dicarbonate or DMDC is a colourless liquid with a sharp odour. Its primary use is as a beverage preservative and or processing aid or sterilant , and acts by inhibiting the enzymes acetate kinase and L-glutamic acid decarboxylase...
.
Methyl carbamate is used by the textile industry to manufacture resins to be applied on polyester/cotton blend fabrics as durable-press finishes.
N-Methyl carbamates are widely used as insecticides.