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a mild sedative-hypnotic drug (trade name Placidyl) (同)Placidyl

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/26 13:45:20」(JST)

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Ethchlorvynol/ˌɛθklɒrˈvaɪnɒl/ 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. 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

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

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

^ ^a ^b ^c "Erowid Ethchlorvynol Vault". Erowid. 12 January 2007. Retrieved 17 April 2014.
^ "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.
^ ^a ^b A. Bavley, W.M. McLamore, U.S. Patent 2,746,900 Hypnotic Agent and Method of Making the Same (1956)
^ 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.
^ McLamore, W. M.; P'an, S. Y.; Bavley, A. (1955). "Hypnotics and Anticonvulsants. Ii. Halogenated Tertiary Acetylenic Carbinols". Journal of Organic Chemistry 20: 109–117. doi:10.1021/jo01119a018.

Electronic Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations Food and Drug Administration. Accessed 12 December 2005 (UTC)

UpToDate Contents

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1. 血液灌流 hemoperfusion

English Journal

An unusual trichloroethanol fatality attributed to sniffing trichloroethylene.

Jones GR, Singer PP.SourceOffice of the Chief Medical Examiner, 7007 - 116 Street NW, Edmonton, Alberta, Canada T6H 5R8. graham.jones@gov.ab.ca
Journal of analytical toxicology.J Anal Toxicol.2008 Mar;32(2):183-6.
We report the death of a 28-year-old man due to sniffing a contact cement containing trichloroethylene. Initial testing revealed the presence of 80 mg/L trichloroethanol in cardiac blood, and the death was ruled as being due to trichloroethanol toxicity resulting from chloral hydrate ingestion. Howe
PMID 18334104

Drug-induced pulmonary edema and acute respiratory distress syndrome.

Lee-Chiong T Jr, Matthay RA.SourceSection of Pulmonary Medicine, Department of Medicine, National Jewish Medical and Research Center, 1400 Jackson Street, Denver, CO 80206, USA. lee-chiongt@njc.org
Clinics in chest medicine.Clin Chest Med.2004 Mar;25(1):95-104.
Noncardiogenic pulmonary edema, and, to a lesser extent, acute respiratory distress syndrome (ARDS), are common clinical manifestations of drug-induced lung diseases. Clinical features and radiographic appearances are generally indistinguishable from other causes of pulmonary edema and ARDS. Typical
PMID 15062601

Loxapine intoxication: case report and literature review.

Mazzola CD, Miron S, Jenkins AJ.SourceThe Office of the Cuyahoga County Coroner, Cleveland, Ohio 44106, USA.
Journal of analytical toxicology.J Anal Toxicol.2000 Oct;24(7):638-41.
Loxapine is a dibenzoxazepine tricyclic compound used to treat schizophrenia in the United States since 1976. Metabolism includes demethylation to its primary metabolite, amoxapine. There are few documented reports of the disposition of loxapine in deaths due to overdose. This report discusses the o
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Japanese Journal

Effects of Vegetable Oils on the Biological Disposition of Ethchlorvynol. II. The Effects on the Brain Distribution of Ethchlorvynol in Rat

Chemical & pharmaceutical bulletin 27(1), 264-267, 1979-01-25
NAID 110003623440

Effects of vegetable oils on the biological disposition of ethchlorvynol. II. The effects on the brain distribution of ethchlorvynol in rat.

Chemical and Pharmaceutical Bulletin 27(1), 264-267, 1979
NAID 130003940577

Effects of Vegetable Oils on the Biological Disposition of Ethchlorvynol. I. The Effects on the Distribution of Ethchlorvynol in Rat

Chemical & pharmaceutical bulletin 26(4), 1257-1260, 1978-04-25
NAID 110003623120

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Ethchlorvynol
Systematic (IUPAC) name
	1-chloro-3-ethylpent-1-en-4-yn-3-ol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Legal status	DE: Anlage II; US: Schedule IV;
Routes of; administration	Oral
Pharmacokinetic data
Protein binding	35–50%
Identifiers
CAS Number	113-18-8
ATC code	N05CM08
PubChem	CID 5281077
IUPHAR/BPS	7180
DrugBank	DB00189
ChemSpider	4444534
UNII	6EIM3851UZ
KEGG	D00704
ChEMBL	CHEMBL591
Chemical data
Formula	C7H9ClO
Molar mass	144.598 g/mol
	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+ ; Key:ZEHYJZXQEQOSON-AATRIKPKSA-N ;
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