DIETHYL ETHER

General Information

Synonyms: ETHER, ETHYL ETHER
Chemical Names: DIETHYL ETHER; DIETHYL OXIDE; 1,1'-OXYBISETHANE
CAS number: 60-29-7
Functional Class: Food Additives
EXTRACTION_SOLVENT

From apps.who.int

Evaluations

Evaluation year: 1979
ADI: NO ADI ALLOCATED
Meeting: 23
Specs Code: R,T (1990)
Report: TRS 648-JECFA 23/21
Tox Monograph: NOT PREPARED
Specification: COMPENDIUM ADDENDUM 8/FNP 52 Add.8/53 (2000). R; FAO JECFA Monographs 1 vol.1/465

From apps.who.int

Computed Descriptors

Download SDF
2D Structure
CID3283
IUPAC Nameethoxyethane
InChIInChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
InChI KeyRTZKZFJDLAIYFH-UHFFFAOYSA-N
Canonical SMILESCCOCC
Molecular FormulaC4H10O
Wikipediaether

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight74.123
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Complexity11.1
CACTVS Substructure Key Fingerprint A A A D c c B g I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A A A A A A A C g g A I C A A A A B A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area9.2
Monoisotopic Mass74.073
Exact Mass74.073
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count5
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9766
Human Intestinal AbsorptionHIA+0.9967
Caco-2 PermeabilityCaco2+0.7268
P-glycoprotein SubstrateNon-substrate0.6370
P-glycoprotein InhibitorNon-inhibitor0.9278
Non-inhibitor0.9568
Renal Organic Cation TransporterNon-inhibitor0.8576
Distribution
Subcellular localizationLysosome0.6388
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8521
CYP450 2D6 SubstrateNon-substrate0.8724
CYP450 3A4 SubstrateNon-substrate0.7433
CYP450 1A2 InhibitorNon-inhibitor0.7090
CYP450 2C9 InhibitorNon-inhibitor0.9179
CYP450 2D6 InhibitorNon-inhibitor0.9576
CYP450 2C19 InhibitorNon-inhibitor0.9175
CYP450 3A4 InhibitorNon-inhibitor0.9904
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8927
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9007
Non-inhibitor0.9304
AMES ToxicityNon AMES toxic0.9133
CarcinogensCarcinogens 0.7956
Fish ToxicityHigh FHMT0.5419
Tetrahymena Pyriformis ToxicityLow TPT0.9864
Honey Bee ToxicityHigh HBT0.8204
BiodegradationReady biodegradable0.5079
Acute Oral ToxicityIII0.8693
Carcinogenicity (Three-class)Non-required0.5586

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-0.0458LogS
Caco-2 Permeability1.4193LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4711LD50, mol/kg
Fish Toxicity3.2831pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.3848pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureOral ; inhalation
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.
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.
Toxicity ValuesLD50: 996 mg/kg (Intravenous, Mouse) LD50: 2420 mg/kg (Intraperitoneal, Mouse) LD50: 1213 mg/kg (Oral, Rat) LC50: 186 mg/L (Inhalation, Mouse)
Lethal Dose30 mL for an adult human.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsDiethyl ether causes CNS depression. Death due to respiratory depression may result from severe and prolonged exposure. (T36)
TreatmentThere is no antidote for diethyl ether poisoning, thus treatment is symptomatic and supportive.
Reference
  1. Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60.[11054601 ]
  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. 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 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassEthers
Intermediate Tree NodesNot available
Direct ParentDialkyl ethers
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsDialkyl ether - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound 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.

From ClassyFire

Targets

Target Details

Alcohol dehydrogenase 1A

General Function:
Zinc ion binding
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular Weight:
39858.37 Da
References
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

Alcohol dehydrogenase 1B

General Function:
Zinc ion binding
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular Weight:
39854.21 Da
References
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

Alcohol dehydrogenase 1C

General Function:
Zinc ion binding
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular Weight:
39867.27 Da
References
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

Alcohol dehydrogenase 4

General Function:
Zinc ion binding
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular Weight:
40221.335 Da
References
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

Alcohol dehydrogenase 6

General Function:
Zinc ion binding
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular Weight:
39088.335 Da
References
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

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
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

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
  1. Wikipedia. Diethyl ether. Last Updated 25 June 2009.: http://en.wikipedia.org/wiki/Ethyl_ether [3296835 ]
Target Details

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
  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 ]

From T3DB