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.com	Micromedex 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) In general: ℞ (Prescription only)
Identifiers
IUPAC name (1-ethynylcyclohexyl)carbamate
CAS Number	126-52-3
PubChem CID	3284
IUPHAR/BPS	7325
DrugBank	DB01031
ChemSpider	3169
UNII	IAN371PP48
KEGG	D00703
ChEBI	CHEBI:4884
ChEMBL	ChEMBL1576
CompTox Dashboard (EPA)	DTXSID7023013
ECHA InfoCard	100.004.355
Chemical and physical data
Formula	C9H13NO2
Molar mass	167.208 g·mol^−1
3D model (JSmol)	Interactive image
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) Key:GXRZIMHKGDIBEW-UHFFFAOYSA-N
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Ethinamate has been replaced by other medicines (particularly benzodiazepines), and it is not available in the Netherlands, the United States or Canada.

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.[1][2]

References

1. H. Pfeiffer, K. Junkman, U.S. Patent 2,816,910 (1957)
2. H. Emde, W. Grimme, DE 1021843 (1953)