Ethchlorvynol

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Ethchlorvynol
Ethchlorvynol.svg
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 YesY
N05CM08
PubChem CID 5281077
DrugBank DB00189 N
ChemSpider 4444534 YesY
UNII 6EIM3851UZ YesY
KEGG D00704 YesY
ChEMBL CHEMBL591 YesY
Chemical data
Formula C7H9ClO
144.598 g/mol
 N (what is this?)  (verify)

Ethchlorvynol/ˌɛθklɒrˈvnɒl/ is a sedative and hypnotic medication developed by Pfizer in the 1950s.[3] In the United States it was sold by Abbott Laboratories under the tradename Placidyl.[1] Placidyl was available in 200 mg., 500 mg., and 750 mg. strength capsules. 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. Street names for the drug [clarification needed] may have included "jelly-bellies" or "pickles", reflecting their appearance.[citation needed] Abbott discontinued production in 1999,[1] after which Placidyl was available for about a year in the United States. Although, theoretically, ethchlorvynol could be manufactured for sale in the United States by another pharmaceutical company (subject to FDA approval of such manufacture), no pharmaceutical company has chosen to do so.

Use and effects[edit]

Ethchlorvynol DOJ.jpg

Ethchlorvynol was used to treat insomnia, but prescriptions for the drug had fallen significantly by 1990, as other hypnotics that were considered safer (i.e., less likely to result in overdose) became much more common. 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, 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. 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.

Placidyl can be addictive. After prolonged use, withdrawal symptoms may include convulsions, hallucinations, and amnesia. As with most hypnotics, Placidyl was indicated for use in the treatment of insomnia for a short period of time (a week or two). However, it was nonetheless not uncommon for doctors to prescribe Placidyl (and other hypnotics) for extended periods of time.

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[edit]

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]

Ethchlorvynol synthesis.png

References[edit]

  1. ^ a b c "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. ^ a b 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.  edit
  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)