Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:22 UTC
Update Date2014-12-24 20:21:25 UTC
Accession NumberT3D0255
Identification
Common NameEthyl ether
ClassSmall Molecule
DescriptionDiethyl 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. (8)
Compound Type
  • Ether
  • Household Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,1'-Oxybisethane
1,1'-oxydiethane
1-Ethoxyethane
3-Oxapentane
Aether
Anaesthetic ether
Anesthesia ether
Diethyl ether
Diethylaether
Ether
Ethoxyethane
Ethyl oxide
Pronarcol
Solvent ether
Sulfuric ether
Sulfuric ether, anesthetic ether
Chemical FormulaC4H10O
Average Molecular Mass74.122 g/mol
Monoisotopic Mass74.073 g/mol
CAS Registry Number60-29-7
IUPAC Nameethoxyethane
Traditional Namediethyl ether
SMILESCCOCC
InChI IdentifierInChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
InChI KeyInChIKey=RTZKZFJDLAIYFH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDialkyl ethers
Alternative Parents
Substituents
  • Dialkyl ether
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-116.3°C
Boiling Point34.6°C
Solubility60.4 mg/mL at 25°C [RIDDICK,JA et al. (1986)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility39 g/LALOGPS
logP1.12ALOGPS
logP0.84ChemAxon
logS-0.28ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.51 m³·mol⁻¹ChemAxon
Polarizability9.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-ff3ce446c6b7cd58b202View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-003r-9000000000-539b7fc110138db40d75View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-ff3ce446c6b7cd58b202View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-003r-9000000000-539b7fc110138db40d75View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-10d91e40ecddd76245c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-c5f86cff2dabe5301e60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-bb91b9271db21e8dca93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-9a0648894838d71c9ed2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-285d2b728c775ce1c04dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-1f10875191ded34dd6deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-4927709fe9ae0353e92eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0560-9000000000-190d02146f42b3306a37View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4)
Mechanism of ToxicityDiethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (8, 1)
MetabolismDiethyl 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. (4)
Toxicity ValuesLD50: 996 mg/kg (Intravenous, Mouse) (9) LD50: 2420 mg/kg (Intraperitoneal, Mouse) (9) LD50: 1213 mg/kg (Oral, Rat) (2) LC50: 186 mg/L (Inhalation, Mouse) (3)
Lethal Dose30 mL for an adult human. (4)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDiethyl ether is used as a common solvent and has been used as a general anesthetic. It can also be found in recreational drug use. (8)
Minimum Risk LevelNot Available
Health EffectsDiethyl ether causes CNS depression. Death due to respiratory depression may result from severe and prolonged exposure. (4)
SymptomsInhalation may result in dizziness, giddiness, euphoria, drowsiness, salivation, and CNS depression. Diethyl ether is also a skin and eye irritant. (4)
TreatmentThere is no antidote for diethyl ether poisoning, thus treatment is symptomatic and supportive. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID3283
ChEMBL IDCHEMBL16264
ChemSpider ID3168
KEGG IDC13240
UniProt IDNot Available
OMIM ID
ChEBI ID35702
BioCyc IDCPD-5702
CTD IDNot Available
Stitch IDEthyl ether
PDB IDNot Available
ACToR ID1704
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0255.pdf
General References
  1. 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 ]
  2. Nelson DL, Gehlert DR: Central nervous system biogenic amine targets for control of appetite and energy expenditure. Endocrine. 2006 Feb;29(1):49-60. [16622292 ]
  3. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [11054601 ]
  4. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  5. USEPA (2007). High Production Volume Information System (HPVIS): Ethane, 1,1'-oxybis- (60-29-7).
  6. European Chemicals Bureau (2007). IUCLID Dataset: Diethyl Ether (CAS # 60-29-7).
  7. Verschueren K (2001). Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. New York, NY: John Wiley & Sons.
  8. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
  9. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular Weight:
39858.37 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular Weight:
39854.21 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular Weight:
39867.27 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular Weight:
40221.335 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular Weight:
39088.335 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
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.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular Weight:
41480.985 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
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.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular Weight:
39723.945 Da
References
  1. 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 ]
  2. Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]