4637 Ethyl carbamate Ethyl carbamate (also known as urethane) is an ester of carbamic acid. It is not a component of polyurethanes. Urethane can be produced by the reaction of ammonia with ethyl chloroformate or by heating urea nitrate and ethyl alcohol. It was first prepared in the mid 1800’s. Ethyl carbamate was used as an antineoplastic agent in the treatment of multiple myeloma before it was found in 1943 to be toxic, carcinogenic and largely ineffective. Japanese usage in medical injections continued and from 1950 to 1975. Ethyl carbamate has now been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anesthetic for animals. Studies have shown that most, if not all, yeast-fermented alcoholic beverages contain traces of ethyl carbamate (15 ppb to 12 ppm). Other foods and beverages prepared by means of fermentation also contain ethyl carbamate. For example, bread has been found to contain 2 ppb while as much as 20 ppb has been found in some samples of soy sauce. “Natural” ethyl carbamate is formed during distillation from natural precursors such as cyanide, urea, citrulline and other N-carbamoyl compounds. 51-79-6 5641 C3H7NO2 White powder 48.5 - 50 °C 183 °C 4.8E+005 mg/L (at 15 °C) Ingestion; Inhalation; Injection Ethyl carbamate is genotoxic and a potent carcinogen. It exerts its effects through the formation of DNA adducts (via its vinyl carbamate epoxide metabolite) that induce choromosomal aberrations, micronuclei and sister chromatid exchange. It also tends to induce specific mutations in the Kras oncogene in codon 61 of exon 2 including A:T transversions and A-->G transitions in the second base and A-->T transversions in the third base. Ethyl carbamate is rapidly metabolized in the body with 95% being eliminated as carbon dioxide. It is readily absorbed from the gastrointestinal tract and the skin. Metabolism is mediated by cytochrome P450 2E1. Metabolites of ethyl carbamate include N-hydroxyethylcarbamate, alpha-hydroxyethylcarbamate and vinyl carbamate. After conjugation, N-hydroxyethylcarbamate is excreted in the urine, alpha-hydroxyethyl carbamate is metabolized to ammonia and CO2 and vinyl carbamate is converted to vinyl carbamate epoxide. The vinyl carbamate epoxide is thought to be the metabolite that is responsible for the carcinogenic properties of ethyl carbamate based on its ability to form etheno-DNA adducts (A15086) LD50 in rodents of 2g/kg (ingestion) 2A, probably carcinogenic to humans. (L135) Small quantities of ethyl carbamate are still used in laboratories as an anesthetic for animals. Ethyl carbamate is found in many alcoholic beverages, especially distilled spirits. >0.3 mg/kg/day for lung cancer Ethyl carbamate can cause cancer. Acute exposure can cause severe eye irritation and skin irritation. Urethane is toxic to kidneys, the nervous system, liver, gastrointestinal tract. Repeated or prolonged exposure to urethane can produce organ damage. Acute exposure to eyes causes redness, watering, and itching. EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. 2014-09-05T17:10:48Z 2026-04-03T07:36:09Z Ethyl_carbamate C01537 17967 DB04827 true CCOC(N)=O C3H7NO2 InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5) JOYRKODLDBILNP-UHFFFAOYSA-N 89.0932 89.047678473 Endogenous Solid -0.15 HMDB31219 CHEMBL462547 5439 <p>Norton A. Cashen, &#8220;Method of producing anhydrous crystalline reaction products of formaldehyde and methyl-, ethyl carbamate.&#8221; U.S. Patent US4002668, issued July, 1973.</p> CHEM003543 DTXSID9021427 ethyl carbamate