Ethinamate

Ethinamate

Systematic (IUPAC) name
(1-ethynylcyclohexyl)carbamate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral
Identifiers
CAS number	126-52-3
ATC code	None
PubChem	CID 3284
DrugBank	DB01031
ChemSpider	3169 Y
UNII	IAN371PP48 Y
KEGG	D00703 Y
ChEBI	CHEBI:4884 Y
ChEMBL	CHEMBL1576 Y
Chemical data
Formula	C9H13NO2
Mol. mass	167.205 g/mol
SMILES	eMolecules & PubChem
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
Y(what is this?)  (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Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.

Chemistry

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

There is some reason to believe that the intermediate used in the synthesis of ethinamate is in itself a depressant and is actually the active metabolite of ethinamate.