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Ethchlorvynol

From Wikipedia, the free encyclopedia
Group of stereoisomers

Pharmaceutical compound
Ethchlorvynol
Structural formula
Ball-and-stick model of the ethchlorvynol molecule
Clinical data
Pronunciation/ˌɛθklɔːrˈvnɒl/
ETH-klor-VY-nol
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding35–50%
Identifiers
  • 1-chloro-3-ethylpent-1-en-4-yn-3-ol
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.239.078Edit this at Wikidata
Chemical and physical data
FormulaC7H9ClO
Molar mass144.60 g·mol−1
3D model (JSmol)
  • Cl[C@H]=CC(C#C)(O)CC
  • InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+ checkY
  • Key:ZEHYJZXQEQOSON-AATRIKPKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ethchlorvynol, sold under the brand namePlacidyl, is aGABA receptor agonist andcentral nervous systemdepressant withanxiolytic,sedative, andhypnotic developed byPfizer in the 1950s.[4] Originally identified in 1956 byresearch chemists atAbbott Laboratories in theUnited States, ethchlorvynol becameFDA-approved drug[2] Thedosage form was always as asoftgelcap, 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 withinbenzodiazepine family (with drugs such as Librium and Valium);[5][2] by the end of 2001, ethchlorvynol reserves had dried up in the United States.

Uses

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Ethchlorvynol was indicated to treatinsomnia, 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.[citation needed]

Availability

[edit]

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.[citation needed]

Adverse effects

[edit]

Along with expected sedative effects of relaxation and drowsiness, adverse reactions to ethchlorvynol include skin rash, faintness, restlessness, andeuphoria. Early adjustment side effects may include nausea and vomiting, numbness, blurred vision, stomach pains, and temporary dizziness.[citation needed]

Occasional deaths would occur when addicted persons would try to inject the drug directly into a vein or an artery. Ethchlorvynol is not compatible withintravenous injection, and serious injury (including the loss of limbs due to vascular injury) or death can occur when it is used in this manner.[citation needed]

Overdose

[edit]

There are no specific antidotes available for ethchlorvynol, and treatment is supportive with protocols resembling those for the treatment ofbarbiturate 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]

Withdrawal

[edit]

Regular use of anyGABAA receptor agonist can result indrug dependency andphysical addiction; conversely,abrupt cessation of long-term of such substances cna potentially cause lethaldrug withdrawal effects resembling the effects ofwithdrawal from alcohol, possible uponcessation, orbarbiturate withdrawal, and the convulsions, hallucinations, andamnesiaincluding convulsions, hallucinations, andamnesia. 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 ofElvis Presley, and resulted in Supreme Court JusticeWilliam Rehnquist as well asSteven Tyler ofAerosmith both being hospitalized for detox.[6]

Chemistry

[edit]

Ethchlorvynol is a member of the class of sedative-hypnotic carbinols, which includesmethylparafynol andtert-amyl alcohol. It is not abenzodiazepine,carbamate, orbarbiturate, 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 anethynylation reaction using lithiumacetylide and 1-chloro-1-penten-3-one inliquid ammonia, followed by acidicwork-up.[4][7]

Theanalogous compound consisting of acarbamate derived from thehydroxy group was investigated and was shown to have a slower onset, longer duration, and increased potency, but was not developed commercially.[citation needed]

References

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  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. Retrieved16 August 2023.
  2. ^abc"Erowid Ethchlorvynol Vault". Erowid. 12 January 2007. Retrieved17 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 fromthe original(PDF) on 10 September 2015. Retrieved17 April 2014.
  4. ^abUS 2746900, Bavley A, McLamore WM, "Hypnotic Agent and Method of Making the Same", issued 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. Retrieved21 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.

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