{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447908931 | IUPAC_name = 3-methylpent-1-yn-3-ol | image = Methylpentynol.svg | image_class = skin-invert-image | alt = Structural formula | width = 150 | image2 = Methylpentynol molecule spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model of methylpentynol | width2 = 190
<!--Clinical data--> | tradename = Oblivon | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_BR = C1 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = Withdrawn | routes_of_administration = By mouth
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 77-75-8 | ATC_prefix = N05 | ATC_suffix = CM15 | PubChem = 6494 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = B017BC5B1N | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 21106516
<!--Chemical data--> | C=6 | H=10 | O=1 | smiles = CCC(C)(C#C)O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = QXLPXWSKPNOQLE-UHFFFAOYSA-N | synonyms = Methylparafynol }}
'''Methylpentynol''' (also known as '''methylparafynol''', trade names '''Dormison''', '''Atemorin''', '''Oblivon''') is a tertiary pentynol with hypnotic/sedative and anticonvulsant effects and an exceptionally low therapeutic index. It was discovered by Bayer in 1913<ref>{{ cite patent | country = DE | status = patent | number = 289800 | gdate = 1913-11-30 | assign1 = Bayer, Leverkusen | title = Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen }}</ref> and was used shortly thereafter for the treatment of insomnia, but its use was quickly phased out in response to newer drugs with far more favorable safety profiles.<ref>{{cite journal | vauthors = Hirsh HL, Orsinger WH | title = Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity | journal = American Practitioner and Digest of Treatment | volume = 3 | issue = 1 | pages = 23–6 | date = January 1952 | pmid = 14903452 }}</ref><ref>{{cite journal | vauthors = Schaffarzick RW, Brown BJ | title = The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols | journal = Science | volume = 116 | issue = 3024 | pages = 663–5 | date = December 1952 | pmid = 13028241 | doi = 10.1126/science.116.3024.663 | bibcode = 1952Sci...116..663S }}</ref><ref>{{cite journal | vauthors = Herz A | title = [A new type of hypnotic; unsaturated tertiary carbinols; experimental studies on therapeutic use of 3-methyl-pentin-ol-3 (methylparafynol)] | journal = Arzneimittel-Forschung | volume = 4 | issue = 3 | pages = 198–9 | date = March 1954 | pmid = 13159700 }}</ref>
The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative.<ref>{{cite journal | vauthors = Weaver LC, Alexander WM, Abreu BE | title = Anticonvulsant activity of compounds related to methylparafynol | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 131 | pages = 116–22 | date = April 1961 | pmid = 13783544 }}</ref> The drug was quickly overshadowed at that point by benzodiazepines and is no longer sold anywhere.<ref>{{cite book | first = Richard Devenport | last = Hines | name-list-style = vanc | title = The Pursuit of Oblivion | date = 2002 | pages = 327 }}</ref>
==Synthesis== Methylpentynol is prepared by reaction of butanone (MEK) with sodium acetylide in liquid ammonia. This reaction must be done in anhydrous conditions and in an inert atmosphere. ==Applications== As building block in the synthesis of: # Phthalofyne (1,2-Benzenedicarboxylic acid, mono(1-ethyl-1-methyl-2-propynyl) ester) [131-67-9] # Anansiol (1-ethyl-1-methylprop-2-ynyl carbamate) [302-66-9] # Bason ( 2-Bromoethynyl-2-butanol) [2028-52-6]
== See also == *Clocental<ref>{{cite patent | inventor = Grimene W, Emde H | country = DE | number = 959485 | gdate = 1957 }}</ref> *Ethchlorvynol
== References == {{reflist}}
{{alcohols}} {{Hypnotics and sedatives}} {{GABAAR PAMs}}
Category:Alkynols Category:Anticonvulsants Category:GABAA receptor positive allosteric modulators Category:Tertiary alcohols Category:Abandoned drugs {{Anticonvulsant-stub}} {{Sedative-stub}}