<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3005</id>
  <title>T3D2963</title>
  <common-name>Ethinamate</common-name>
  <description>Ethinamate 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.</description>
  <cas>126-52-3</cas>
  <pubchem-id>3284</pubchem-id>
  <chemical-formula>C9H13NO2</chemical-formula>
  <weight>167.094630</weight>
  <appearance>White powder.</appearance>
  <melting-point>94-96°C</melting-point>
  <boiling-point>120°C at 3.00E+00 mm Hg</boiling-point>
  <density nil="true"/>
  <solubility>2500 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Rapidly absorbed following oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The 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.</mechanism-of-toxicity>
  <metabolism>Hepatic.Half Life: 2.5 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used for the short-term treatment of insomnia, however, it generally has been replaced by other sedative-hypnotic agents.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.</health-effects>
  <symptoms>Symptoms of overdose include shortness of breath or slow or troubled breathing, slow heartbeat, severe weakness, chronic confusion, slurred speech, and staggering.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:12Z</created-at>
  <updated-at type="dateTime">2026-04-03T12:57:02Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Ethinamate</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07832</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>4884</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Ethinamate</stitch-id>
  <drugbank-id>DB01031</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>NC(=O)OC1(CCCCC1)C#C</moldb-smiles>
  <moldb-formula>C9H13NO2</moldb-formula>
  <moldb-inchi>InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)</moldb-inchi>
  <moldb-inchikey>GXRZIMHKGDIBEW-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">167.205</moldb-average-mass>
  <moldb-mono-mass type="decimal">167.094628665</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.2</logp>
  <hmdb-id>HMDB15165</hmdb-id>
  <chembl-id>CHEMBL1576</chembl-id>
  <chemspider-id>3169</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to&lt;br /&gt;
Schering AG, Germany.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002326</chemdb-id>
  <dsstox-id>DTXSID7023013</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00024040</susdat-id>
  <iupac>1-ethynylcyclohexyl carbamate</iupac>
</compound>
