ContaminantDB: Ethyl carbamate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-09-05 17:10:48 UTC

Update Date

2026-04-03 07:36:09 UTC

Accession Number

CHEM003543

Identification

Common Name

Ethyl carbamate

Class

Small Molecule

Description

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 Ethyl carbamate has now been withdrawn from pharmaceutical use.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.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2A
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anesthetic, Intravenous
Antineoplastic Agent
Carcinogen
Ester
Ether
Food Toxin
Lachrymator
Metabolite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Carbamic acid ethyl ester	ChEBI
Carbamate ethyl ester	Generator
Ethyl carbamic acid	Generator
Aethylcarbamat	HMDB
Aethylurethan	HMDB
Carbamate, ethyl	HMDB
Carbamic acid, ethyl ester	HMDB
Estane 5703	HMDB
Ethyl aminoformate	HMDB
Ethyl ester OF carbamic acid	HMDB
Ethyl urethan	HMDB
Ethyl urethane	HMDB
Ethylcarbamate	HMDB
Ethylester kyseliny karbaminove	HMDB
Ethylurethan	HMDB
Ethylurethane	HMDB
Leucethane	HMDB
Leucothane	HMDB
NH2COOC2H5	HMDB
NSC 746	HMDB
O-Ethyl carbamate	HMDB
O-Ethyl urethane	HMDB
O-Ethylurethane	HMDB
Pracarbamin	HMDB
Pracarbamine	HMDB
U-compound	HMDB
Uretan	HMDB
Uretan etylowy	HMDB
Uretano	HMDB
Urethan	HMDB
Urethane	HMDB
Urethane + ethanol (combination)	HMDB
Urethane, inn	HMDB
Ethyl carbamate	ChEBI

Chemical Formula

C₃H₇NO₂

Average Molecular Mass

89.093 g/mol

Monoisotopic Mass

89.048 g/mol

CAS Registry Number

51-79-6

IUPAC Name

ethyl carbamate

Traditional Name

urethane

SMILES

CCOC(N)=O

InChI Identifier

InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)

InChI Key

JOYRKODLDBILNP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Not Available

Direct Parent

Carboximidic acids and derivatives

Alternative Parents

Substituents

Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester (CHEBI:17967 )
a small molecule (URETHAN )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

mutagen

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder

Experimental Properties

Property	Value
Melting Point	48.5 - 50 °C
Boiling Point	183 °C
Solubility	4.8E+005 mg/L (at 15 °C)

Predicted Properties

Property	Value	Source
Water Solubility	371 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-0.054	ChemAxon
logS	0.62	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	20.84 m³·mol⁻¹	ChemAxon
Polarizability	8.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01r7-9000000000-ba57e1f4b939a6bb2c1c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01r7-9000000000-4905daa85aa870eff5d7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01r7-9000000000-ba57e1f4b939a6bb2c1c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01r7-9000000000-4905daa85aa870eff5d7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9000000000-e97e597e9d87bdb17da9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-5187886e237ef9d66a60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01oy-9000000000-8c895ae06181b5b4338d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-ec38f306aca381823adb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-f2310b881ad089adcd93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-143896eea6847dbb32c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-51c772011dee8070de89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000m-9000000000-df4925907c41e53b12db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-719d518ee46e1ba1c4f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-1abfabaf6ce4ac254e95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-6bd0c888cfe6b3835c30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fd9f25340762315b4515	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01r7-9000000000-dbaaf921e6f73cb42292	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ingestion; Inhalation; Injection

Mechanism of Toxicity

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.

Metabolism

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 (3)

Toxicity Values

Not Available

Lethal Dose

LD50 in rodents of 2g/kg (ingestion)

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (4)

Uses/Sources

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.

Minimum Risk Level

>0.3 mg/kg/day for lung cancer

Health Effects

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.

Symptoms

Acute exposure to eyes causes redness, watering, and itching.

Treatment

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.

Concentrations

Not Available

External Links

DrugBank ID

DB04827

HMDB ID

HMDB0031219

FooDB ID

FDB003243

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Norton A. Cashen, “Method of producing anhydrous crystalline reaction products of formaldehyde and methyl-, ethyl carbamate.” U.S. Patent US4002668, issued July, 1973.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15790490

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24386880

3. Lijinsky W, Taylor HW: Carcinogenesis in Sprague-Dawley rats of N-nitroso-N-alkylcarbamate esters. Cancer Lett. 1976 May;1(5):275-9.

4. Lijinsky W, Reuber MD: Studies of a deuterium isotope effect in carcinogenesis by N-nitroso-N-alkylurethanes in rats. Cancer Lett. 1982 Sep;16(3):273-9.

5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Ethyl carbamate (CHEM003543)

Structure for CHEM003543: Ethyl carbamate