Methylpentynol: Difference between revisions

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{{drugbox
{{Drugbox
| IUPAC_name       = 3-methylpent-1-yn-3-ol
| Verifiedfields = changed
| image             = Methylpentynol.png
| Watchedfields = changed
| CAS_number        = 77-75-8
| verifiedrevid = 447908931
| ATC_prefix        = N05
| IUPAC_name = 3-methylpent-1-yn-3-ol
| ATC_suffix        = CM15 
| image = Meparfynol.png
| PubChem          = 6494
 
| DrugBank          =
<!--Clinical data-->
| C=6|H=10|O=1
| tradename Oblivon
| molecular_weight = 98.143 g/mol
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| bioavailability  =
| pregnancy_US = <!-- A / B            / C / D / X -->
| protein_bound    =
| pregnancy_category =   
| metabolism        =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| elimination_half-life =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| excretion        =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_status =
| pregnancy_category=   
| routes_of_administration =
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| 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     =  
| routes_of_administration =  
}}


'''Methylpentynol''' ('''Methylparafynol''', '''Dormison''', '''Atemorin''') is a [[hypnotic]]/[[sedative]] with [[anticonvulsant]] effects. It was previously used for the treatment of [[insomnia]] but has been replaced by newer drugs with better safety profiles.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> 
<!--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


{{pharmacology-stub}}


<!--Chemical data-->
| C=6 | H=10 | O=1
| molecular_weight = 98.143 g/mol
| smiles            = CCC(C)(C#C)O
| InChI            = 1/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3
| InChIKey          = QXLPXWSKPNOQLE-UHFFFAOYAI
| 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
}}
__NOTOC__
{{SI}}
{{CMG}}
==Overview==
'''Methylpentynol''' ('''Methylparafynol''', '''Dormison''', '''Atemorin''') is a [[Alcohol#tertiary|tertiary]] [[hexanol]] with [[hypnotic]]/[[sedative]] and [[anticonvulsant]] effects. It was discovered by Bayer in 1913 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.
To make meparfynol proper, the alcohol must be reacted with [[phosgene]] followed by ammonia to form the [[carbamate]] (see patent). Also, ethynylation of cyclohexanone is one of the preferred analogs
==References==
==References==
{{reflist|2}}
{{reflist|2}}


{{Hypnotics and sedatives}}
{{Hypnotics and sedatives}}
{{WikiDoc Sources}}
 
[[Category:Anticonvulsants]]
[[Category:Drug]]

Latest revision as of 16:42, 20 August 2015

Methylpentynol
Clinical data
Trade namesOblivon
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
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Chemical and physical data
FormulaC6H10O
Molar mass98.143 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Methylpentynol (Methylparafynol, Dormison, Atemorin) is a tertiary hexanol with hypnotic/sedative and anticonvulsant effects. It was discovered by Bayer in 1913 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. To make meparfynol proper, the alcohol must be reacted with phosgene followed by ammonia to form the carbamate (see patent). Also, ethynylation of cyclohexanone is one of the preferred analogs

References