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T3D0255 - Ethyl ether

Record Information
Version 1.0
Creation Date 2009-03-06 18:58:22 UTC
Update Date 2013-04-25 08:33:29 UTC
Accession Number T3D0255
Identification
Common Name Ethyl ether
Description Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor. It is the most common member of a class of chemical compounds known generically as ethers. Diethyl ether is used as a common solvent and has been used as a general anesthetic. It can also be found in recreational drug use. (V371)
Compound Type
  • Organic Compound
  • Solvent
  • Ether
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. 1,1'-Oxybisethane
  2. 1,1'-oxydiethane
  3. 1-Ethoxyethane
  4. 1-ethoxyethane (ACD/Name 4.0)
  5. 3-Oxapentane
  6. Aether
  7. Anaesthetic ether
  8. Anesthesia ether
  9. Anesthetic ether
  10. Diaethylaether
  11. Diaethylaether [german]
  12. Diethyl ether
  13. diethyl ether (ACD/Name 4.0)
  14. Diethyl ether [anaesthetics, volatile]
  15. Diethyl oxide
  16. Dwuetylowy eter
  17. Dwuetylowy eter [polish]
  18. Etere etilico
  19. Etere etilico [italian]
  20. Ether
  21. Ether ethylique
  22. Ether ethylique [french]
  23. Ether [jan]
  24. Ethoxyethane
  25. Ethyl ether
  26. Ethyl ether anhydrous a.c.s.
  27. Ethyl ether usp/acs
  28. Ethyl ether, tech
  29. Ethyl ether, tech.
  30. Ethyl oxide
  31. Oxyde d'ethyle
  32. Oxyde d'ethyle [french]
  33. Pronarcol
  34. Solvent ether
  35. Sulfuric ether
  36. Sulfuric ether, anesthetic ether
Chemical Formula C4H10O
Average Molecular Weight 74.1216
Monoisotopic Molecular Weight 74.073164942
Chemical IUPAC Name
diethyl ether
CAS Registry Number 60-29-7
SMILES
CCOCC
InChI Identifier
InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
InChI Key InChIKey=RTZKZFJDLAIYFH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organooxygen Compounds
Class Ethers
Sub Class Dialkyl Ethers
Direct Parent Dialkyl Ethers
Alternative Parents Not Available
Molecular Framework Aliphatic Acyclic Compounds
Substituents Not Available
External Descriptors
  • a small molecule(Cyc)
  • ether(ChEBI)
DrugBank ID Not Available
PubChem Compound ID 3283 Link_out
KEGG ID C13240 Link_out
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 35702 Link_out
BioCyc ID CPD-5702 Link_out
CTD ID Not Available
Stitch ID Ethyl ether Link_out
PDB ID Not Available
ACToR ID 1704
Wikipedia Link Not Available
Physical Properties
Appearance Not Available
Melting Point -116.3 C
Solubility 60.4 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]
Predicted LogP 0.8381653443333331
Toxicity Profile
Route of Exposure Oral (R383) ; inhalation (R383)
Mechanism of Action Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
Metabolism Diethyl ether can be absorbed following ingestion and inhalation, and is then rapidly distributed to the brain and fatty tissues. Diethyl ether is not metabolized in humans and is excreted mainly in expired air. (R383)
Toxicity Values LD50: 996 mg/kg (Intravenous, Mouse) (V372) LD50: 2420 mg/kg (Intraperitoneal, Mouse) (V372) LD50: 1213 mg/kg (Oral, Rat) (V374) LC50: 186 mg/L (Inhalation, Mouse) (V373)
Lethal Dose 30 mL for an adult human. (R383)
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Diethyl ether is used as a common solvent and has been used as a general anesthetic. It can also be found in recreational drug use. (V371)
Minimum Risk Level Not Available
Health Effects Diethyl ether causes CNS depression. Death due to respiratory depression may result from severe and prolonged exposure. (R383)
Symptoms Inhalation may result in dizziness, giddiness, euphoria, drowsiness, salivation, and CNS depression. Diethyl ether is also a skin and eye irritant. (R383)
Treatment There is no antidote for diethyl ether poisoning, thus treatment is symptomatic and supportive. (R383)
References
General References
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V372 — USEPA (2007). High Production Volume Information System (HPVIS): Ethane, 1,1'-oxybis- (60-29-7).
  • V373 — European Chemicals Bureau (2007). IUCLID Dataset: Diethyl Ether (CAS # 60-29-7).
  • V374 — Verschueren K (2001). Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. New York, NY: John Wiley & Sons.
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]
  • R383 — Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.

Targets

1. Alcohol dehydrogenase 1A

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P07327 Link_out
Gene: ADH1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]

2. Alcohol dehydrogenase 1B

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P00325 Link_out
Gene: ADH1B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]

3. Alcohol dehydrogenase 1C

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P00326 Link_out
Gene: ADH1C Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]

4. Alcohol dehydrogenase 4

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P08319 Link_out
Gene: ADH4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]

5. Alcohol dehydrogenase 6

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P28332 Link_out
Gene: ADH6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]

6. Alcohol dehydrogenase class 4 mu/sigma chain

Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P40394 Link_out
Gene: ADH7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]

7. Alcohol dehydrogenase class-3

Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (V371, V375)
UniProt ID: P11766 Link_out
Gene: ADH5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • V371 — Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  • V375 — Normann PT, Ripel A, Morland J. Diethyl ether inhibits ethanol metabolism in vivo by interaction with alcohol dehydrogenase. Alcohol Clin Exp Res. 1987 Apr;11(2):163-6. [3296835 Link_out]