Ethinamate

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Ethinamate
Ethinamate.svg
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • CA: Schedule IV
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.355 Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO2
Molar mass167.205 g/mol g·mol−1
3D model (JSmol)
  (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.[citation needed]

Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.[citation needed]

Synthesis[edit]

Ethinamate (1-ethynylcyclohexanone carbamate) is synthesized by combining acetylene with cyclohexanone and then transforming the resulting product 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)