Ethinamate

Quality 0.50 · 2 views · Updated 2 months ago

Pharmaceutical drug

title: "Ethinamate" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hypnotics", "sedatives", "carbamates", "ethynyl-compounds", "gabaa-receptor-positive-allosteric-modulators"] description: "Pharmaceutical drug" topic_path: "general/hypnotics" source: "https://en.wikipedia.org/wiki/Ethinamate" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Pharmaceutical drug ::

::data[format=table title="Infobox drug"]

Field	Value
verifiedrevid	443740995
IUPAC_name	(1-ethynylcyclohexyl)carbamate
image	Ethinamate structure.svg
image_class	skin-invert-image
tradename	Valmid, Valamin
Drugs.com
pregnancy_category	C
legal_BR	B1
legal_BR_comment
legal_CA	Schedule IV
legal_US	Schedule IV
legal_DE	Anlage II
legal_UK	Class C
legal_status	Rx-only
routes_of_administration	Oral
elimination_half-life	2.5 hours
IUPHAR_ligand	7325
CAS_number_Ref
CAS_number	126-52-3
ATC_prefix	none
PubChem	3284
DrugBank_Ref
DrugBank	DB01031
ChemSpiderID_Ref
ChemSpiderID	3169
UNII_Ref
UNII	IAN371PP48
KEGG_Ref
KEGG	D00703
ChEBI_Ref
ChEBI	4884
ChEMBL_Ref
ChEMBL	1576
C	9
smiles	O=C(OC1(C#C)CCCCC1)N
StdInChI_Ref
StdInChI	1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)
StdInChIKey_Ref
StdInChIKey	GXRZIMHKGDIBEW-UHFFFAOYSA-N
::

Ethinamate, marketed as Valmid in the United States and Valamin in Australia, is a central nervous system depressant of the carbamate drug class. It was formerly prescribed as a hypnotic for the short-term treatment of insomnia. The drug has a rapid onset of action, a short elimination half-life of around 2.5 hours, and a correspondingly brief duration of effect. Prolonged use leads to drug tolerance, drug dependence, and diminished efficacy after seven days of continuous use.

Availability

Ethinamate was introduced by German drug company Schering AG in 1957, marketed as as a sleeping pill with "barbiturate-like" effects and reduced risk of fatality in drug overdose compared to barbiturate overdose. Ethinamate was commonly prescribed in Germany, the United States, Australia, Canada, the Netherlands, and much of Europe. Ethinamate is not known to be available in any country. Despite being available in the U.S. until 1982, ethinamate largely fell out of favor by the 1960s, as contemporary novel tranquilizers with less tolerance and longer duration of action were viewed as more effective – including methaqualone, ethchlorvynol, glutethimide, methyprylon, meprobamate, and the benzodiazepines chlordiazepoxide and diazepam In the United States, ethinamate is now primarily remembered in connection with the toxicology reports on the death of Elvis Presley: it was listed among multiple sedatives detected in his system, and some forensic experts, including Cyril Wecht, later emphasized that polypharmacy was an important factor in the case.

Toxicity and overdose

Ethinamate has a wider therapeutic index and safety profile compared to barbiturates, with drug overdose of the former rarely causing fatality by respiratory depression (as is more likely in barbiturate overdose). Reported cases illustrate that doses as high as 2,800 mg induce temporary loss of consciousness or comatose state, though recovery is possible and likely with supportive care. Activated charcoal may reduce absorption if administered early (25–100 g for adults; 25–50 g in children under 12; 1 g/kg in infants), and hemodialysis can be considered in severe cases.

Adverse effects and safety in pregnancy

Ethinamate's primary effects result from CNS depression, manifesting as a slow heart rate, shallow breathing, and low blood pressure. Minor side effects at therapeutic doses include nausea, vomiting, gastrointestinal upset, and skin rash. Rare hypersensitivity reactions may involve thrombocytopenia purpura, fever, and rashes. Children are more likely than adults to experience paradoxical effects, so the drug was not indicated for individuals under 18.

Hypersensitivity reactions may involve thrombocytopenia purpura, fever, and various skin rashes.

The drug is classified as pregnancy Category C, and is not recommended during pregnancy or breastfeeding due to insufficient evidence regarding potential teratogenic effects. Animal studies suggest porphyrinogenic potential in vivo.

Chemistry and synthesis

The compound is synthesized by reacting acetylene with cyclohexanone to form 1-ethynylcyclohexanol. This intermediate is then converted into a carbamate through reaction with phosgene and ammonia. Small amounts of lithium or similar reagents may be used to facilitate the initial acetylene reaction. ::figure[src="https://upload.wikimedia.org/wikipedia/commons/1/14/Ethinamate_synthesis.png"] ::

Ethinamate, whose molecular structure is known as 1-ethynylcyclohexanyneone carbamate is an odorless, white crystalline powder. It is typically formulated as 500 mg tablets for oral administration, with an adult dose of one tablet at bedtime; two tablets may be taken if necessary. Children are more prone to paradoxical effects and the drug is not indicated for individuals under 18.The compound is synthesized by reacting acetylene with cyclohexanone to form 1-ethynylcyclohexanol. This intermediate is then converted into a carbamate through reaction with phosgene and ammonia. Small amounts of lithium or similar reagents may be used to facilitate the initial acetylene reaction.

After ingestion, ethinamate is metabolized to the active compound 4-hydroxyethinamate, which is eliminated in urine with a half-life of approximately 2.5 hours.

References

(31 March 2023). "RDC Nº 784 – Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
"Victoria Museum of Pharmacology".
"Ethinamate (Valmid, Valamin): Overview". PubChem.
(1979). "Forensic Toxicology: Controlled Substances and Dangerous Drugs". Springer US.
(2 August 2017). "The Death of Elvis". Memphis Magazine.
"Esters of carbamic acid and a method of making same".
"Verfahren zur Herstellung des Allophanats des 1-AEthinylcyclohexanols-(1)".

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::