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Details

Stereochemistry ACHIRAL
Molecular Formula C4H6O
Molecular Weight 70.0898
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Vinyl ether

SMILES

C=COC=C

InChI

InChIKey=QYKIQEUNHZKYBP-UHFFFAOYSA-N
InChI=1S/C4H6O/c1-3-5-4-2/h3-4H,1-2H2

HIDE SMILES / InChI
Vinyl ether (divinyl ether) is a clear colorless liquid with a characteristic odor. Less dense than water. Vapors heavier than air. Toxic by inhalation. Leake and Chen in 1930 demonstrated that vinyl ether possessed anaesthetic properties, and in 1931 a purer and more stable product was prepared in the research laboratories of Merck and Co. by Ruigh and Major and was used as ananaesthetic on dogs by Knoefel, Guedel, and Leake. These investigators found that dogs were more easily anaesthetized by vinyl ether than by chloroform. They also found that the period of recovery was rapid and free from vomiting; moreover, they did not notice any significant pathological effect on the various organs.The first experiments on human beings were conducted in 1933 by Gelfan and Bell. The first extensive account of vinyl ether anaesthesia in man was published in 1934, when Goldschmidt et al. reported having used it in operations in 461 mixed cases. In all these cases vinyl ether appeared to have no undesirable effect on respiration, the circulation, the liver, or the kidneys. Vinyl ether was widely used in Europe and North America for at least 30 years, until it was replaced by halothane. Vinyl ether was marketed under the name of Vinethine in the United States, Vinesthine in the United Kingdom, and Vinydan in continental Europe. Vinyl ether outlasted many of the inhalation agents introduced in recent years, and served a very useful purpose until safer, non-flammable agents, became available in the mid1960s.

Approval Year

Doses

Doses

DosePopulationAdverse events​
3 mL single, respiratory
Recommended
Dose: 3 mL
Route: respiratory
Route: single
Dose: 3 mL
Sources:
unhealthy, 3-9
n = 2210
Health Status: unhealthy
Condition: dental extractions
Age Group: 3-9
Population Size: 2210
Sources:
Other AEs: Convulsions...
Other AEs:
Convulsions (5 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Convulsions 5 patients
3 mL single, respiratory
Recommended
Dose: 3 mL
Route: respiratory
Route: single
Dose: 3 mL
Sources:
unhealthy, 3-9
n = 2210
Health Status: unhealthy
Condition: dental extractions
Age Group: 3-9
Population Size: 2210
Sources:
PubMed

PubMed

TitleDatePubMed
An allyltitanium derived from acrolein 1,2-dicyclohexylethylene acetal and (eta(2)-propene)Ti(O-i-Pr)(2) as a chiral propionaldehyde homoenolate equivalent that reacts with imines with excellent stereoselectivity. An efficient and practical access to optically active gamma-amino carbonyl compounds.
2001 Apr 18
Plasmalogens, phospholipase A2, and docosahexaenoic acid turnover in brain tissue.
2001 Apr-Jun
Effect of fluorinated groups on photooxidative stability of polymeric protectives applied on marble.
2001 Nov-Dec
Reactive brominating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: disparate utilization of sodium halides in the production of alpha-halo fatty aldehydes.
2002 Feb 15
C-phosphanyl-C-chloroiminium salts as electrophilic carbene synthetic equivalents.
2002 Oct 7
Phospholipid plasmalogen, a surrogate marker of oxidative stress, is associated with increased cardiovascular mortality in patients on renal replacement therapy.
2004 Apr
Catalytic asymmetric claisen rearrangement in natural product synthesis: synthetic studies toward (-)-xeniolide F.
2005 Dec 8
Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids.
2005 Feb
Hydration of vinyl ether groups by unsaturated glycoside hydrolases and their role in bacterial pathogenesis.
2007 Dec
Shotgun lipidomics identifies a paired rule for the presence of isomeric ether phospholipid molecular species.
2007 Dec 26
Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco.
2007 Jan
The investigation of protein adsorption behaviors on different functionalized polymers films.
2007 Jun
Reduction of divinyl ether-containing polyunsaturated fatty acids in transgenic potato plants.
2007 Mar
Organocatalytic claisen rearrangement: theory and experiment.
2007 May 25
Separation of intact plasmalogens and all other phospholipids by a single run of high-performance liquid chromatography.
2007 Nov 1
Dipole-LUMO/dipolarophile-HOMO controlled asymmetric cycloadditions of carbonyl ylides catalyzed by chiral Lewis acids.
2007 Oct 11
How to improve the storage stability of aqueous polymeric film coatings.
2008 Feb 18
Sheddable coatings for long-circulating nanoparticles.
2008 Jan
Patents

Patents

Sample Use Guides

In the blood, anaesthesia is produced with a remarkably small concentration; in dogs this is 28 mg per 100 ccm.
Route of Administration: Respiratory
Name Type Language
Vinyl ether
WHO-DD  
Systematic Name English
DIVINYL ETHER
MI  
Systematic Name English
Vinyl ether [WHO-DD]
Common Name English
DIVINYL ETHER [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QN01AA02
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
WHO-ATC N01AA02
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
Code System Code Type Description
CAS
109-93-3
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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WIKIPEDIA
Divinyl ether
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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ChEMBL
CHEMBL2105883
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DRUG CENTRAL
3645
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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FDA UNII
2H2T044E11
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SMS_ID
100000076712
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EPA CompTox
DTXSID5074555
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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DRUG BANK
DB13690
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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MESH
C100195
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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ECHA (EC/EINECS)
203-720-5
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PUBCHEM
8024
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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EVMPD
SUB15697MIG
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
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MERCK INDEX
m4697
Created by admin on Fri Dec 15 14:57:57 GMT 2023 , Edited by admin on Fri Dec 15 14:57:57 GMT 2023
PRIMARY Merck Index