Ethinamate

Summary

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 dependence.[citation needed]

Ethinamate
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • (1-ethynylcyclohexyl)carbamate
CAS Number
  • 126-52-3 checkY
PubChem CID
  • 3284
IUPHAR/BPS
  • 7325
DrugBank
  • DB01031 checkY
ChemSpider
  • 3169 checkY
UNII
  • IAN371PP48
KEGG
  • D00703 checkY
ChEBI
  • CHEBI:4884 checkY
ChEMBL
  • ChEMBL1576 checkY
CompTox Dashboard (EPA)
  • DTXSID7023013 Edit this at Wikidata
ECHA InfoCard100.004.355 Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO2
Molar mass167.208 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.[citation needed]

It is a schedule IV substance in the United States.[2]

Synthesis edit

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.[3][4]

 

References edit

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ 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.
  3. ^ US 2816910, Pfeiffer H, Junkman K, "Esters of carbamic acid and a method of making same", issued 17 December 1957, assigned to Schering AG 
  4. ^ DE 1021843, Emde H, Grimme W, "Verfahren zur Herstellung des Allophanats des 1-AEthinylcyclohexanols-(1)", issued 2 January 1958, assigned to Rheinpreussen AG