Ethinamate

Ethinamate

Systematic (IUPAC) name
(1-ethynylcyclohexyl)carbamate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Legal status	CA: Schedule IV DE: Anlage II (Prohibited) ℞ (Prescription only)
Routes of administration	Oral
Identifiers
CAS Number	126-52-3 Y
ATC code	none
PubChem	CID: 3284
IUPHAR/BPS	7325
DrugBank	DB01031 Y
ChemSpider	3169 Y
UNII	IAN371PP48 Y
KEGG	D00703 Y
ChEBI	CHEBI:4884 Y
ChEMBL	CHEMBL1576 Y
Chemical data
Formula	C9H13NO2
Molecular mass	167.205 g/mol
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
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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Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.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.