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Ethinamate
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Ethinamate

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Ethinamate
Ethinamate structure.svg
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • (1-ethynylcyclohexyl)carbamate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.355
Chemical and physical data
Formula C9H13NO2
Molar mass 167.208 g·mol−1
3D model (JSmol)
  • O=C(OC1(C#C)CCCCC1)N
  • InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11) checkY
  • Key:GXRZIMHKGDIBEW-UHFFFAOYSA-N checkY
  (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Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.

It is a schedule IV substance in the United States.

Synthesis

Ethinamate (1-ethynylcyclohexanone carbamate) is synthesized by combining acetylene with cyclohexanone to make 1-ethynylcyclohexanol, and then transforming this 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.

Ethinamate synthesis.png




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