Tmic
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Record Information
Version2.0
Creation Date2009-07-21 20:28:12 UTC
Update Date2014-12-24 20:25:54 UTC
Accession NumberT3D2963
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.
Compound Type
  • Amine
  • Carbamate
  • Drug
  • Ester
  • Ether
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-Ethynylcyclohexanol carbamate
Aethinyl-cyclohexyl-carbamat
Ethinamat
Ethinamatum
Ethinamic acid
Ethinimate
Etinamate
Etinamato
USAF EL-42
Valamin
Valmid
Chemical FormulaC9H13NO2
Average Molecular Mass167.205 g/mol
Monoisotopic Mass167.095 g/mol
CAS Registry Number126-52-3
IUPAC Name1-ethynylcyclohexyl carbamate
Traditional Nameethinamate
SMILESOC(=N)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 KeyInChIKey=GXRZIMHKGDIBEW-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)
LogP1.2
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-115ca538c5db7623cd36View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-3530aac44af3672b4ea8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-115ca538c5db7623cd36View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-3530aac44af3672b4ea8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9400000000-b2399bc8d370f3c24953View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-1900000000-eae16bf8bad39a8aa79bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-4900000000-5017ae578b8cb02cd66dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-9100000000-cd1eedbdd6d6fcbfa22eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-9800000000-e408920834450f49d3feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9500000000-877c16eefea2f5a15d9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b9a9228e0ee207499b99View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0arv-9100000000-713c62aa52e71fc3560aView in MoNA
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01031
HMDB IDHMDB15165
PubChem Compound ID3284
ChEMBL IDCHEMBL1576
ChemSpider ID3169
KEGG IDC07832
UniProt IDNot Available
OMIM ID
ChEBI ID4884
BioCyc IDNot Available
CTD IDNot Available
Stitch IDEthinamate
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkEthinamate
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. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular Weight:
28870.0 Da
References
  1. Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [1460006 ]
General Function:
Zinc ion binding
Specific Function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
References
  1. Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [1460006 ]