T3DB: Ethyl ether

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (8)XML

Targets (8)

Record Information

Version

2.0

Creation Date

2009-03-06 18:58:22 UTC

Update Date

2014-12-24 20:21:25 UTC

Accession Number

T3D0255

Identification

Common Name

Ethyl ether

Class

Small Molecule

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. (8)

Compound Type

Ether
Household Toxin
Industrial/Workplace Toxin
Lachrymator
Organic Compound
Solvent
Synthetic Compound

Chemical Structure

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

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 Formula

C₄H₁₀O

Average Molecular Mass

74.122 g/mol

Monoisotopic Mass

74.073 g/mol

CAS Registry Number

60-29-7

IUPAC Name

ethoxyethane

Traditional Name

diethyl ether

SMILES

CCOCC

InChI Identifier

InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3

InChI Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Dialkyl ethers

Alternative Parents

Hydrocarbon derivatives

Substituents

Dialkyl ether
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ether (CHEBI:35702 )
a small molecule (DIETHYLETHER )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

non-polar solvent

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-116.3°C
Boiling Point	34.6°C
Solubility	60.4 mg/mL at 25°C [RIDDICK,JA et al. (1986)]
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	39 g/L	ALOGPS
logP	1.12	ALOGPS
logP	0.84	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.51 m³·mol⁻¹	ChemAxon
Polarizability	9.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-ff3ce446c6b7cd58b202	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-003r-9000000000-539b7fc110138db40d75	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-ff3ce446c6b7cd58b202	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-003r-9000000000-539b7fc110138db40d75	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-10d91e40ecddd76245c4	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-c5f86cff2dabe5301e60	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-bb91b9271db21e8dca93	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-9000000000-9a0648894838d71c9ed2	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-285d2b728c775ce1c04d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-1f10875191ded34dd6de	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-4927709fe9ae0353e92e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-d8e55135cb66b23d1ad9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-9000000000-c9d15b2dd1e8ebea8b07	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-bca7098270d845cb82bd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-cdbb8e496fb16f106ace	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006t-9000000000-627bc9130f9c128d29c5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2cd1209dd668634b9425	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0560-9000000000-190d02146f42b3306a37	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4)

Mechanism of Toxicity

Diethyl ether inhibits alcohol dehydrogenase. This slows down the metabolism of ethanol and also inhibits the metabolism of other drugs requiring oxidative metabolism. (8, 1)

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. (4)

Toxicity Values

LD50: 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 Dose

30 mL for an adult human. (4)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

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. (8)

Minimum Risk Level

Not Available

Health Effects

Diethyl ether causes CNS depression. Death due to respiratory depression may result from severe and prolonged exposure. (4)

Symptoms

Inhalation may result in dizziness, giddiness, euphoria, drowsiness, salivation, and CNS depression. Diethyl ether is also a skin and eye irritant. (4)

Treatment

There is no antidote for diethyl ether poisoning, thus treatment is symptomatic and supportive. (4)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

35702

BioCyc ID

CPD-5702

CTD ID

Not Available

Stitch ID

Ethyl ether

PDB ID

Not Available

ACToR ID

1704

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D0255.pdf

General References

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 ]
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 ]
Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [11054601 ]
Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
USEPA (2007). High Production Volume Information System (HPVIS): Ethane, 1,1'-oxybis- (60-29-7).
European Chemicals Bureau (2007). IUCLID Dataset: Diethyl Ether (CAS # 60-29-7).
Verschueren K (2001). Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. New York, NY: John Wiley & Sons.
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]
Drugs.com [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Alcohol dehydrogenase 1A

General Function:: Zinc ion binding
Specific Function:: Not Available
Gene Name:: ADH1A
Uniprot ID:: P07327
Molecular Weight:: 39858.37 Da

References

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

2. Alcohol dehydrogenase 1B

General Function:: Zinc ion binding
Specific Function:: Not Available
Gene Name:: ADH1B
Uniprot ID:: P00325
Molecular Weight:: 39854.21 Da

References

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

3. Alcohol dehydrogenase 1C

General Function:: Zinc ion binding
Specific Function:: Not Available
Gene Name:: ADH1C
Uniprot ID:: P00326
Molecular Weight:: 39867.27 Da

References

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

4. Alcohol dehydrogenase 4

General Function:: Zinc ion binding
Specific Function:: Not Available
Gene Name:: ADH4
Uniprot ID:: P08319
Molecular Weight:: 40221.335 Da

References

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

5. Alcohol dehydrogenase 6

General Function:: Zinc ion binding
Specific Function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular Weight:: 39088.335 Da

References

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

6. Alcohol dehydrogenase class 4 mu/sigma chain

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

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

7. Alcohol dehydrogenase class-3

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

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 ]
Wikipedia. Diethyl ether. Last Updated 25 June 2009. [Link]

Target Details

8. Transient receptor potential cation channel subfamily A member 1

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

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 ]

Ethyl ether (T3D0255)

Structure for T3D0255: Ethyl ether

Targets

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