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Ethyl carbamate

Ethyl carbamate
Structural formula of ethyl carbamate
Ethyl Carbamate 3D Balls.png
Names
IUPAC name
Ethyl carbamate
Other names
Urethane
Identifiers
51-79-6 YesY
3D model (Jmol) Interactive image
Interactive image
3DMet B00312
ChEBI CHEBI:17967 YesY
ChEMBL ChEMBL462547 YesY
ChemSpider 5439 YesY
DrugBank DB04827 YesY
ECHA InfoCard 100.000.113
EC Number 200-123-1
KEGG C01537 YesY
MeSH Urethane
PubChem 5641
RTECS number FA8400000
UNII 3IN71E75Z5 YesY
UN number 2811
Properties
C3H7NO2
Molar mass 89.09 g·mol−1
Appearance White crystals
Density 1.056 g cm−3
Melting point 46 to 50 °C (115 to 122 °F; 319 to 323 K)
Boiling point 182 to 185 °C (360 to 365 °F; 455 to 458 K)
0.480 g cm−3 at 15 °C
log P -0.190(4)
Vapor pressure 1.3 kPa at 78 °C
Acidity (pKa) 13.58
0.5206015862 D
Hazards
Main hazards Harmful if swallowed

May cause cancer
Toxic T
R-phrases R45
S-phrases S45, S53
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 92 °C (198 °F; 365 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

May cause cancer

Ethyl carbamate (also called urethane) is a chemical compound with the molecular formula C3H7NO2 first prepared in the nineteenth century. Structurally, it is an ester of carbamic acid. Despite its common name, it is not a component of polyurethanes.

Ethyl carbamate is a white crystalline substance produced by heating urea nitrate and ethyl alcohol or by the action of ammonia on ethyl chloroformate.

Ethyl carbamate has been produced commercially in the United States for many years. It has been used as an antineoplastic agent and for other medicinal purposes but this ended after it was discovered to be carcinogenic in 1943. However, Japanese usage in medical injections continued and from 1950 to 1975 an estimated 100 million 2 ml ampules of 7 to 15% solutions of ethyl carbamate were injected into patients as a co-solvent in water for dissolving water-insoluble analgesics used for post-operation pain. These doses were estimated by Nomura (Cancer Research, 35, 2895–2899, October 1975) to be at levels that are carcinogenic in mice. This practice was stopped in 1975. "This regrettable medical situation appears to have involved the largest number (millions) of humans exposed to the largest doses of a pure carcinogen that is on record" (Japanese Journal of Cancer Research, 82, 1323–1324, December 1991). The author, U.S. cancer researcher James A. Miller, called for studies to determine the effects on Japanese cancer rates to be performed but apparently none were ever done.

Prior to World War II, ethyl carbamate saw relatively heavy use in the treatment of multiple myeloma before it was found to be toxic, carcinogenic and largely ineffective. By US FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anesthetic for animals.

Ethyl carbamate was upgraded to a Group 2A carcinogen by IARC in 2007.

Formerly, crosslinking agents for permanent press textile treatments were synthesized from ethyl carbamate.


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