Ethinamate (CHEM002326)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:12 UTC
Update Date2016-11-09 01:08:44 UTC
Accession NumberCHEM002326
Identification
Common NameEthinamate
ClassSmall Molecule
DescriptionEthinamate is a short-acting sedative-hypnotic medication used to treat insomnia. Regular use leads to tolerance, and it is usually not effective for more than 7 days. Structurally, it does not resemble the barbituates, but it shares many effects with this class of drugs; the depressant effects of ethinamate are, however, generally milder than those of most barbiturates.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Carbamate
  • Drug
  • Ester
  • Ether
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Ethynylcyclohexanol carbamateChEBI
Aethinyl-cyclohexyl-carbamatChEBI
EthinamatumChEBI
EtinamatoChEBI
ValmidKegg
1-Ethynylcyclohexanol carbamic acidGenerator
Ethinamic acidGenerator
EthinamatHMDB
EthinimateHMDB
EtinamateHMDB
USAF el-42HMDB
ValaminHMDB
ValmidateHMDB
ValamidHMDB
1-EthynylcyclohexylcarbamateHMDB
Chemical FormulaC9H13NO2
Average Molecular Mass167.205 g/mol
Monoisotopic Mass167.095 g/mol
CAS Registry Number126-52-3
IUPAC Name1-ethynylcyclohexyl carbamate
Traditional Nameethinamate
SMILESNC(=O)OC1(CCCCC1)C#C
InChI IdentifierInChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)
InChI KeyGXRZIMHKGDIBEW-UHFFFAOYSA-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
  • Carbamic acid ester
  • Carbonic acid derivative
  • Acetylide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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 RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point94-96°C
Boiling Point120°C at 3.00E+00 mm Hg
Solubility2500 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP1.09ALOGPS
logP1.54ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.57 m³·mol⁻¹ChemAxon
Polarizability17.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-115ca538c5db7623cd36Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-3530aac44af3672b4ea8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-115ca538c5db7623cd36Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-3530aac44af3672b4ea8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9400000000-b2399bc8d370f3c24953Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-1900000000-eae16bf8bad39a8aa79bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-4900000000-5017ae578b8cb02cd66dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-9100000000-cd1eedbdd6d6fcbfa22eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-9800000000-e408920834450f49d3feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9500000000-877c16eefea2f5a15d9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b9a9228e0ee207499b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-10552185ed182d4ba1e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9700000000-cd8eef43ebf47b3d3b7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-9313282cbda800790a68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0avl-2900000000-d0731a549bbc943d745eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9500000000-35acbd59dd232e271712Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ff48c45d4a47d2073ba7Spectrum
MSMass Spectrum (Electron Ionization)splash10-0arv-9100000000-713c62aa52e71fc3560aSpectrum
Toxicity Profile
Route of ExposureRapidly absorbed following oral administration.
Mechanism of ToxicityThe mechanism of action is not known. However, studies have shown that ethinamate inhibits carbonic anhydrases I and II (J Biol Chem. 1992 Dec 15;267(35):25044-50). This inhibition by ethinamate is not sufficiently strong, however, to implicate carbonic anhydrases I and II in the mechanism of action.
MetabolismHepatic. Half Life: 2.5 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed for the short-term treatment of insomnia, however, it 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 shortness of breath or slow or troubled breathing, slow heartbeat, severe weakness, chronic confusion, slurred speech, and staggering.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01031
HMDB IDHMDB0015165
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthinamate
Chemspider ID3169
ChEBI ID4884
PubChem Compound ID3284
Kegg Compound IDC07832
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to
Schering AG, Germany.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2885000
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=5252608
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=560472