Ethinamate

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
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)
  • UK: Class C
  • US: Schedule IV
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (1-ethynylcyclohexyl)carbamate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.355
Chemical and physical data
FormulaC9H13NO2
Molar mass167.208 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OC1(C#C)CCCCC1)N
InChI
  • InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11) Y
  • Key:GXRZIMHKGDIBEW-UHFFFAOYSA-N Y
  (verify)

Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.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.[1]

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.[2][3]

References
  1. Lowry WT, Garriot JC (1979). "Ethinamate". Forensic Toxicology: Controlled Substances and Dangerous Drugs. Boston, MA: Springer US. p. 215. ISBN 978-1-4684-3444-6.
  2. US 2816910, Pfeiffer H, Junkman K, "Esters of carbamic acid and a method of making same", issued 17 December 1957, assigned to Schering AG
  3. DE 1021843, Emde H, Grimme W, "Verfahren zur Herstellung des Allophanats des 1-AEthinylcyclohexanols-(1)", issued 2 January 1958, assigned to Rheinpreussen AG



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