methylpentynol

{{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

| tradename = Oblivon

| pregnancy_AU =

| pregnancy_category =

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{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}}

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Withdrawn

| routes_of_administration = By mouth

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| 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

| 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{{ cite patent | country = DE | status = patent | number = 289800 | gdate = 1913-11-30 | assign1 = Bayer, Leverkusen | title = Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen }} 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.{{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 }}{{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 }}{{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 }}

The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative.{{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 }} The drug was quickly overshadowed at that point by benzodiazepines and is no longer sold anywhere.{{cite book | first = Richard Devenport | last = Hines | name-list-style = vanc | title = The Pursuit of Oblivion | date = 2002 | pages = 327 }}