Ethinamate

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Ethinamate
Ethinamate.svg
Systematic (IUPAC) name
(1-ethynylcyclohexyl)carbamate
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Legal status Prescription only
Routes Oral
Identifiers
CAS number 126-52-3
ATC code None
PubChem CID 3284
DrugBank DB01031
ChemSpider 3169 YesY
UNII IAN371PP48 YesY
KEGG D00703 YesY
ChEBI CHEBI:4884 YesY
ChEMBL CHEMBL1576 YesY
Chemical data
Formula C9H13NO2 
Mol. mass 167.205 g/mol
 YesY (what is this?)  (verify)

Ethinamate (Valamin, Valmid) is a short-acting carbamate-derivative sedative-hypnotic medication used to treat insomnia. Regular use leads to drug tolerance, and it is usually not effective for more than 7 days. Prolonged use can lead to dependency.

Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.

Chemistry[edit]

Ethinamate (1-ethynylcyclohexanone carbamate) is synthesized by combining acetylene with cyclohexanone and then transforming the resulting carbinol into a carbamate by the subsequent reaction with phosgene, and later with ammonia. Some lithium metal or similar is used to make the acetylene react with the cyclohexanone in the first step.[1][2]

Ethinamate synthesis.png

References[edit]

  1. ^ H. Pfeiffer, K. Junkman, U.S. Patent 2,816,910 (1957)
  2. ^ H. Emde, W. Grimme, DE 1021843  (1953)