Ethinamate
Pharmaceutical drug
- none
- BR: Class B1 (Psychoactive drugs)[1]
- CA: Schedule IV
- DE: Anlage II (Authorized trade only, not prescriptible)
- UK: Class C
- US: Schedule IV
- In general: ℞ (Prescription only)
- (1-ethynylcyclohexyl)carbamate
- 126-52-3
Y
- 3284
- 7325
- DB01031 Y
- 3169 Y
- IAN371PP48
- D00703 Y
- CHEBI:4884 Y
- ChEMBL1576 Y
- DTXSID7023013
- 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)Y
- Key:GXRZIMHKGDIBEW-UHFFFAOYSA-NY
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Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.[citation needed]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
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
- ^ 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.
- ^ 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.
- ^ US 2816910, Pfeiffer H, Junkman K, "Esters of carbamic acid and a method of making same", issued 17 December 1957, assigned to Schering AG
- ^ 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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