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Record Information
Version2.0
Creation Date2014-09-05 17:10:48 UTC
Update Date2014-12-24 20:26:53 UTC
Accession NumberT3D4583
Identification
Common NameEthyl carbamate
ClassSmall Molecule
DescriptionEthyl 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 Ethyl carbamate has now been withdrawn from pharmaceutical use.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.
Compound Type
  • Amine
  • Anesthetic, Intravenous
  • Antineoplastic Agent
  • Carcinogen
  • Ester
  • Ether
  • Food Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Aethylcarbamat
Aethylurethan
Carbamate, ethyl
Carbamic acid ethyl ester
Carbamic acid, ethyl ester
Carbamidsaeure-aethylester
Estane 5703
Ethyl aminoformate
Ethyl carbamic acid
Ethyl ester of carbamic acid
Ethyl urethan
Ethyl urethane
Ethylcarbamate
Ethylester kyseliny karbaminove
Ethylurethan
Ethylurethane
Leucethane
Leucothane
NH2COOC2H5
NSC 746
O-Ethyl carbamate
O-Ethyl urethane
O-Ethylurethane
Pracarbamin
Pracarbamine
U-Compound
Uretan
Uretan etylowy
Uretano
Urethan
Urethane
Urethane + ethanol (combination)
Urethane, INN
Urethanum
Chemical FormulaC3H7NO2
Average Molecular Mass89.093 g/mol
Monoisotopic Mass89.048 g/mol
CAS Registry Number51-79-6
IUPAC Nameethyl carbamate
Traditional Nameurethane
SMILESCCOC(O)=N
InChI IdentifierInChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
InChI KeyInChIKey=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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassNot Available
Direct ParentCarboximidic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder
Experimental Properties
PropertyValue
Melting Point48.5 - 50 °C
Boiling Point183 °C
Solubility4.8E+005 mg/L (at 15 °C)
LogP-0.15
Predicted Properties
PropertyValueSource
Water Solubility371 g/LALOGPS
logP-0.14ALOGPS
logP-0.054ChemAxon
logS0.62ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.84 m³·mol⁻¹ChemAxon
Polarizability8.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-ba57e1f4b939a6bb2c1cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-4905daa85aa870eff5d7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-ba57e1f4b939a6bb2c1cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-4905daa85aa870eff5d7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-e97e597e9d87bdb17da9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5187886e237ef9d66a60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-9000000000-8c895ae06181b5b4338dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-ec38f306aca381823adbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f2310b881ad089adcd93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-143896eea6847dbb32c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-51c772011dee8070de89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000m-9000000000-df4925907c41e53b12dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-719d518ee46e1ba1c4f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-1abfabaf6ce4ac254e95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-6bd0c888cfe6b3835c30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fd9f25340762315b4515JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-01r7-9000000000-dbaaf921e6f73cb42292JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureIngestion; Inhalation; Injection
Mechanism of ToxicityEthyl 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.
MetabolismEthyl 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 ValuesNot Available
Lethal DoseLD50 in rodents of 2g/kg (ingestion)
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (5)
Uses/SourcesSmall 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 EffectsEthyl 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.
SymptomsAcute exposure to eyes causes redness, watering, and itching.
TreatmentEYES: 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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB04827
HMDB IDHMDB31219
PubChem Compound ID5641
ChEMBL IDCHEMBL462547
ChemSpider ID5439
KEGG IDC01537
UniProt IDNot Available
OMIM ID
ChEBI ID17967
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkEthyl_carbamate
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.

MSDST3D4583.pdf
General References
  1. Lijinsky W, Taylor HW: Carcinogenesis in Sprague-Dawley rats of N-nitroso-N-alkylcarbamate esters. Cancer Lett. 1976 May;1(5):275-9. [828074 ]
  2. 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. [7151047 ]
  3. Forkert PG. "Mechanisms of lung tumorigenesis by ethyl carbamate and vinyl carbamate.". Drug Metab Rev. 2010 May;42(2):355-78. doi: 10.3109/03602531003611915. [20205516 ]
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Forkert PG. "Mechanisms of lung tumorigenesis by ethyl carbamate and vinyl carbamate.". Drug Metab Rev. 2010 May;42(2):355-78. doi: 10.3109/03602531003611915. [20205516 ]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Forkert PG. "Mechanisms of lung tumorigenesis by ethyl carbamate and vinyl carbamate.". Drug Metab Rev. 2010 May;42(2):355-78. doi: 10.3109/03602531003611915. [20205516 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity).Isoform 1 is critical for hindlimb motor control and for the differentiation of amacrine and horizontal cells in the retina. Regulates the expression of PTF1A synergistically with FOXN4 (By similarity).
Gene Name:
RORB
Uniprot ID:
Q92753
Molecular Weight:
53219.385 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.28 uMATG_RORb_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]