Ethchlorvynol

Ethchlorvynol

Clinical data
Pronunciation	/ˌɛθklɔːrˈvaɪnɒl/ ETH-klor-VY-nol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral
ATC code	N05CM08 ( WHO )
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 [2] [3]
Pharmacokinetic data
Protein binding	35–50%
Identifiers
IUPAC name 1-chloro-3-ethylpent-1-en-4-yn-3-ol
CAS Number	113-18-8  Y
PubChem CID	5281077
IUPHAR/BPS	7180
DrugBank	DB00189  N
ChemSpider	4444534  Y
UNII	6EIM3851UZ
KEGG	D00704  Y
ChEMBL	ChEMBL591  Y
CompTox Dashboard (EPA)	DTXSID2023010
ECHA InfoCard	100.239.078
Chemical and physical data
Formula	C7H9ClO
Molar mass	144.60 g·mol−1
3D model (JSmol)	Interactive image
SMILES Cl[C@H]=CC(C#C)(O)CC
InChI InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+ Y Key:ZEHYJZXQEQOSON-AATRIKPKSA-N Y
NY  (what is this?)    (verify)

Ethchlorvynol, sold as Placidyl, is a GABA receptor agonist and central nervous system depressant with anxiolytic, sedative, and hypnotic developed by Pfizer in the 1950s. ^[4] Originally identified in 1956 by research chemists at Abbott Laboratories in the United States, ethchlorvynol became FDA-approved drug ^[2] The dosage form was always as a softgel cap, containing 200 mg, 500 mg, and 750 mg. While the 500 mg and 750 mg strength capsules were for use in reducing sleep latency, the 200 mg strength capsules were intended to be used to re-induce sleep in case of early awakening.^{[ citation needed ]} Abbott discontinued production in 1999 due to problems of the widespread abuse of the substance, and substances within benzodiazepine family (with drugs such as Librium and Valium); ^{[5] [2]} by the end of 2001, ethchlorvynol reserves had dried up in the United States.

Use and effects

Ethchlorvynol was indicated to treat insomnia, and was widely prescribed in the 1960s and 1970s; prescriptions had fallen significantly by 1990, however, as other hypnotics that were considered safer and less dangerous in overdose became more common.

Availability

Ethchlorvynol is no longer prescribed in the United States due to unavailability, but is still available in some countries, and would still be considered legal to possess and use with a valid prescription.

Along with expected sedative effects of relaxation and drowsiness, adverse reactions to ethchlorvynol include skin rash, faintness, restlessness, and euphoria. Early adjustment side effects may include nausea and vomiting, numbness, blurred vision, stomach pains, and temporary dizziness. There are no specific antidotes available for ethchlorvynol, and treatment is supportive with protocols resembling those for the treatment of barbiturate overdose. Overdose may be marked by a variety of symptoms, including confusion, fever, peripheral numbness and weakness, reduced coordination and muscle control, slurred speech, reduced heartbeat, respiratory depression, and in extreme overdoses, coma and death.^{[ citation needed ]}

Discontinuation, withdrawal

Regular use of any GABAA receptor agonist can result in drug dependency and physical addiction; conversely, abrupt cessation of long-term of such substances cna potentiall lethal drug withdrawal effects resembling the effects of withdrawal from alcohol, possible upon cessation, or barbiturate withdrawal, and the cnvulsions, hallucinations, and amnesiaincluding convulsions, hallucinations, and amnesia. Placidyl is indicated for use in the treatment of insomnia for a short period of time, generally ranging from one week to one month. However, it was not uncommon for doctors to prescribe the medication for extended periods of time. In the late 1970s, ethchlorvynol was deemed responsible as one of the agents responsible for the death of Elvis Presley, and resulted in Supreme Court Justice William Rehnquist as well as Steven Tyler of Aerosmith both being hospitalized for detox. Occasional deaths would occur when addicted persons would try to inject the drug directly into a vein or an artery. Ethchlorvynol is not compatible with intravenous injection, and serious injury (including the loss of limbs due to vascular injury) or death can occur when it is used in this manner. ^[6]

Chemistry

Ethchlorvynol is a member of the class of sedative-hypnotic carbinols, which includes methylparafynol and tert-amyl alcohol. It is not a benzodiazepine, carbamate, or barbiturate, and its molecular structure is considerably simpler. The systematic name of ethchlorvynol is usually given as ethyl 2-chlorovinyl ethynyl carbinol or 1-chloro-3-ethylpent-1-en-4-yn-3-ol.^{[ citation needed ]} Its empirical formula is C₇H₉ClO.

Ethchlorvynol is synthesized by an ethynylation reaction using lithium acetylide and 1-chloro-1-penten-3-one in liquid ammonia, followed by acidic work-up. ^{[4] [7]}

The analogous compound consisting of a carbamate derived from the hydroxy group was investigated and was shown to have a slower onset, longer duration, and increased potency, but was not developed commercially.

References

1. Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
2. "Erowid Ethchlorvynol Vault". Erowid. 12 January 2007. Retrieved 17 April 2014.
3. "Annual Statistical Report on Substances Listed in the Convention on Psychotropic Substances of 1971 Form P" (PDF). International Narcotics Control Board (INCB). January 2014. p. 9. Archived from the original (PDF) on 10 September 2015. Retrieved 17 April 2014.
4. US 2746900,Bavley A, McLamore WM,"Hypnotic Agent and Method of Making the Same",issued 8 September 1956 
5. Giannini, A. James (15 January 1997). Drugs of abuse (2nd ed.). Los Angeles, California: Practice Management Information Corp. p. 147. ISBN   9781570660535. LCCN   96024680. OCLC   34906127. OL   986590M . Retrieved 21 May 2025.
6. Glauser FL, Smith WR, Caldwell A, Hoshiko M, Dolan GS, Baer H, Olsher N (January 1976). "Ethchlorvynol (Placidyl)-induced pulmonary edema". Annals of Internal Medicine. 84 (1): 46–8. doi:10.7326/0003-4819-84-1-46. PMID   942681.
7. McLamore WM, P'an SY, Bavley A (1955). "Hypnotics and Anticonvulsants. II. Halogenated Tertiary Acetylenic Carbinols". Journal of Organic Chemistry. 20: 109–117. doi:10.1021/jo01119a018.

External links

• "Electronic Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". Food and Drug Administration. Archived from the original on 28 April 1999. Retrieved 12 December 2005.