Ethchlorvynol (CHEM002140)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:15 UTC
Update Date2016-11-09 01:08:41 UTC
Accession NumberCHEM002140
Identification
Common NameEthchlorvynol
ClassSmall Molecule
DescriptionEthchlorvynol is only found in individuals that have used or taken this drug. It is a sedative and hypnotic drug. It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists. [Wikipedia]Although the exact mechanism of action is unknown, ethchlorvynol appears to depress the central nervous system in a manner similar to that of barbiturates. Barbiturates bind at a distinct binding sites associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PlacidylKegg
EthchlorovynolMeSH
EthchlorvinolMeSH
EthchlorvynolMeSH
Chemical FormulaC7H9ClO
Average Molecular Mass144.600 g/mol
Monoisotopic Mass144.034 g/mol
CAS Registry Number113-18-8
IUPAC Name(1E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
Traditional Nameethchlorvynol
SMILES[H]\C(Cl)=C(\[H])C(O)(CC)C#C
InChI IdentifierInChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+
InChI KeyZEHYJZXQEQOSON-AATRIKPKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ynones. These are organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure RC#C-C(=O)R' (R' not H).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentYnones
Alternative Parents
Substituents
  • Ynone
  • Tertiary alcohol
  • Acetylide
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling Point28.5-30°C
Solubility1.43e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.45ALOGPS
logP1.62ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.64 m³·mol⁻¹ChemAxon
Polarizability14.76 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-198eb76a2aa919525f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3900000000-e1616a7a6e75f2940d8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-9000000000-b25f488adecb3fd0ff42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4900000000-2980fab2cceb6fc96107Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-3900000000-a6b1e1a57494f22868ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9400000000-b1fe9dd4623953d5d8baSpectrum
Toxicity Profile
Route of ExposureOral, rapidly absorbed from gastrointestinal tract.
Mechanism of ToxicityAlthough the exact mechanism of action is unknown, ethchlorvynol appears to depress the central nervous system in a manner similar to that of barbiturates. Barbiturates bind at a distinct binding sites associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
MetabolismAbout 90% of a dose is metabolized in the liver. Some ethchlorvynol may also be metabolized in the kidneys. Ethchlorvynol and metabolites undergo extensive enterohepatic recirculation. Half Life: Plasma half-life is approximately 10 to 20 hours, terminal half-life is 21-100 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed for short-term hypnotic therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.
Minimum Risk LevelNot Available
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
SymptomsSymptoms of overdose include thrombocytopenia.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5281077
Kegg Compound IDC07833
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Bayley, A. and McLamore, W.M.; U.S. Patent 2,746,900; May 22,1956; assigned to Chas.
Pfizer & Co., Inc.

MSDSNot Available
General ReferencesNot Available