Ethchlorvynol

Ethchlorvynol
Systematic (IUPAC) name
1-chloro-3-ethylpent-1-en-4-yn-3-ol
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Oral
Pharmacokinetic data
Protein binding 35–50%
Identifiers
113-18-8 Yes
N05CM08
PubChem CID 5281077
DrugBank DB00189 
ChemSpider 4444534 Yes
UNII 6EIM3851UZ Yes
KEGG D00704 Yes
ChEMBL CHEMBL591 Yes
Chemical data
Formula C7H9ClO
144.598 g/mol
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Ethchlorvynol/ˌɛθklɒrˈvaɪnɒl/ is a sedative and hypnotic medication developed by Pfizer in the 1950s.[3] In the United States Abbott Laboratories used to sell it under the tradename Placidyl.[1] During their heyday, they were known on the street as "jelly-bellies" or "pickles", reflecting their appearance. Since Abbott and Banner Pharmacaps, which manufactured the generic version, discontinued production in 1999,[1] ethchlorvynol has no longer been available in the United States.

Use and effects

Ethchlorvynol has been used to treat insomnia, but has been largely superseded and was only offered where an intolerance or allergy to other drugs exists. It is no longer prescribed in the United States due to unavailability, but it 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, ethchlorvynol can cause skin rashes, faintness, restlessness and euphoria. Early adjustment side effects can include nausea and vomiting, numbness, blurred vision, stomach pains and temporary dizziness. An overdose is marked by confusion, fever, peripheral numbness and weakness, reduced coordination and muscle control, slurred speech, reduced heartbeat, respiratory depression, and in extreme overdoses, coma and death.

It is addictive and after prolonged use can cause withdrawal symptoms including convulsions, hallucinations, and amnesia. Due to these problems, it is unusual for ethchlorvynol to be prescribed for periods exceeding seven days. During the late 1970s, ethchlorvynol was sometimes over-prescribed causing a minor epidemic of persons who quickly became addicted to this powerful drug. 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.[4]

Chemistry

Ethchlorvynol is a member of the class of sedative-hypnotic carbinols, which includes methylparafynol and tert-amyl alcohol. It is not a barbituric acid derivative. 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. Its empirical formula is C7H9ClO.

Ethchlorvynol is synthesized by the reaction of lithium acetylide with 1-chloro-1-penten-3-one in liquid ammonia, followed by acidic work-up.[3][5]

References

  1. ↑ 1.0 1.1 1.2 "Erowid Ethchlorvynol Vault". Erowid. 12 January 2007. Retrieved 17 April 2014.
  2. ↑ "ANNUAL STATISTICAL REPORT ON SUBSTANCES LISTED IN THE CONVENTION ON PSYCHOTROPIC SUBSTANCES OF 1971 FORM P" (PDF). INCB. January 2014. p. 9. Retrieved 17 April 2014.
  3. ↑ 3.0 3.1 A. Bavley, W.M. McLamore, U.S. Patent 2,746,900 Hypnotic Agent and Method of Making the Same (1956)
  4. ↑ Glauser, F. L.; Smith, W. R.; Caldwell, A.; Hoshiko, M.; Dolan, G. S.; Baer, H.; Olsher, N. (1976). "Ethchlorvynol (Placidyl)-induced pulmonary edema". Annals of internal medicine 84 (1): 46–48. doi:10.7326/0003-4819-84-1-46. PMID 942681.
  5. ↑ McLamore, W. M.; P'an, S. Y.; Bavley, A. (1955). Journal of Organic Chemistry 20: 109. doi:10.1021/jo01119a018. Missing or empty |title= (help)