Ethinamate

Ethinamate is a central nervous system (CNS) depressant and carbamate derivative and one of of many non-barbiturate sedative-hypnotic tranquilizers, or "sleeping pills" used to induce sleep, approved and indicated for the short-term treatment of insomnia, taken orally as a pill before bedtime. Mainly sold under the brand name Valmid and Valamin and introduced by Ciba in 1954, ethinamate has a rapid onset of action (inducing sleep immmediately) and a short duration of action due its elimination half-life of one hour.^[2]Relative In these regards, compared to other sleeping pills, ethinamate's profile most resembles that of thez-drug zaleplon.

Ethinamate

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral
ATC code	none
Legal status
Legal status	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)
Identifiers
IUPAC name (1-ethynylcyclohexyl)carbamate
CAS Number	126-52-3 Y
PubChem CID	3284
IUPHAR/BPS	7325
DrugBank	DB01031 Y
ChemSpider	3169 Y
UNII	IAN371PP48
KEGG	D00703 Y
ChEBI	CHEBI:4884 Y
ChEMBL	ChEMBL1576 Y
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) Y Key:GXRZIMHKGDIBEW-UHFFFAOYSA-N Y
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Effects

Both sleeping medications are effective at inducing sleep, but is not likely to keep one asleep due to its metabolization. Thus, patients who primary condition is not falling asleep but staying asleep, longer-acting hypnotics (e.g. methyprylon. glutethimide, chlordiazepoxide, cjlorazepate, diazepam, ethchlorvynol or [[methsqyalone[[ would be more appropriate options. Theoretically, if a user awake ue to disruption or nightmare, they could take another tablet and get back to sleep without feeling groggy or a hangover the upon waking.

Historical use

Ethinamate was prescribed for "short-term" use, typically for only one to two weeks, ranging between seven to fourteen days, due to the rapid development of drug habituation and tolerance to this time. dtime. It may be taken a second time upon early awakening or sleep disruption. For a patient struggling to maintain asleep, longer-release sedative-hypnotic medications such as phenobarbital (a long-acting barbiturate), flurazepam (Dalmane for insomniadiazepam (a long-acting [[benzodiazepine)ethchlorvynol, or [methyprylon (Noludar, discontinued 1975) opposed to maintaing sleep through the .

Efficacy

Habituation and tolerance to ethinamate developed rapidly, often within one week, after which it would lose efficacy in reducing sleep latency. Consequential to this, ethinamate's potential for misuse was low, as recreational drug use would not be possible to achieve full tolerance has been attained. [Drug dependency|Deependence or addiction potential is moderate]] and/or is fairly loweads to drug tolerance, and it is usually not effective for more than 7 days. Prolonged use can lead to dependence.^{[citation needed]}

Ethinamate is not available in the Netherlands, Canada, and the United States any longer,^{[citation needed]} and despite being classified as a Schedule IV controlled medicine available by prescription only, therefore a legal prescription drug, it is incredibly obscure and any prescription would need to be dispensed through a specialty compound pharmacy. Ethinamate has not mass-produced since the 1980s.

It is a schedule IV substance in the United States.^[3]

Chemistry and 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.^[4][5]

Avalability

Ethinimate is not currently, nor has it even been, banned or "illegal" in the United States, i.e. listed as a Schedule I controlled substance per the Controlled Substances Act but was rather voluntarily withdrawn from the market due to declining prescription rates, sales revenues and financial returns. If one were to receive ethinamate in 2025, and be certain of its quality and legitimacy, it would either be a result of compounding or clandestine chemistry.