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Methylpentynol: Difference between revisions

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Revision as of 19:41, 1 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'ChemSpiderID_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikiped← Previous edit Latest revision as of 03:00, 14 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 444937736 | verifiedrevid = 447908931
| IUPAC_name = 3-methylpent-1-yn-3-ol | IUPAC_name = 3-methylpent-1-yn-3-ol
| image = Meparfynol.svg | image = Methylpentynol.svg
| image_class = skin-invert-image
| alt = Structural formula
| image2 = Methylpentynol molecule spacefill.png
| image_class2 = bg-transparent
| alt2 = Space-filling model of methylpentynol
| width2 = 190


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Oblivon
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | 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=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status = Withdrawn
| routes_of_administration = | routes_of_administration = ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
Line 22: Line 31:
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 77-75-8 | CAS_number = 77-75-8
| ATC_prefix = N05 | ATC_prefix = N05
Line 33: Line 43:
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B017BC5B1N | UNII = B017BC5B1N
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21106516


<!--Chemical data--> <!--Chemical data-->
| C=6 | H=10 | O=1 | C=6 | H=10 | O=1
| smiles = CCC(C)(C#C)O
| molecular_weight = 98.143 g/mol
| 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
}} }}


'''Methylpentynol''' ('''Methylparafynol''', '''Dormison''', '''Atemorin''') is a ]/] with ] effects. It was developed in the 1950s,<ref></ref> and was previously used for the treatment of ] but has been replaced by newer drugs with better safety profiles.<ref>HIRSH HL, ORSINGER WH. Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity. ''American Practitioner and Digest of Treatment''. 1952 Jan;3(1):23-6.</ref><ref>SCHAFFARZICK RW, BROWN BJ. The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols. ''Science''. 1952 Dec 12;116(3024):663-5.</ref><ref>HERZ A. A new type of hypnotic; unsaturated tertiary carbinols; experimental studies on therapeutic use of 3-methyl-pentin-ol-3 (methylparafynol). ''Arzneimittelforschung''. 1954 Mar;4(3):198-9.</ref><ref>WEAVER LC, ALEXANDER WM, ABREU BE. Anticonvulsant activity of compounds related to methylparafynol. ''Archives Internationales de Pharmacodynamie et de Therapie''. 1961 Apr 1;131:116-22.</ref> '''Methylpentynol''' ('''Methylparafynol''', '''Dormison''', '''Atemorin''', '''Oblivon''') is a ] pentynol with ]/] and ] effects and an exceptionally low ]. It was discovered by ] 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 ], 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 = | 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 ] 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>
⚫ ==References==
<references />


==Synthesis==
⚫ {{Hypnotics and sedatives}}
Methylpentynol is prepared by reaction of ] (MEK) with sodium ] in liquid ]. This reaction must be done in anhydrous conditions and in an inert atmosphere.
==Applications==
As building block in the synthesis of:
# ] (1,2-Benzenedicarboxylic acid, mono(1-ethyl-1-methyl-2-propynyl) ester)
# ] (1-ethyl-1-methylprop-2-ynyl carbamate)
# Bason ( 2-Bromoethynyl-2-butanol)


== See also ==
⚫ ]
*]<ref>{{cite patent | inventor = Grimene W, Emde H | country = DE | number = 959485 | gdate = 1957 }}</ref>
⚫ ]
*]


⚫ == References ==
{{reflist}}


{{alcohols}}
{{nervous-system-drug-stub}}
⚫ {{Hypnotics and sedatives}}
{{GABAAR PAMs}}


⚫ ]
]
⚫ ]
]
]
]
]
]
]
{{Anticonvulsant-stub}}
{{Sedative-stub}}
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