Methylpentynol: Difference between revisions

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Methylpentynol
Clinical data
Trade names	Oblivon
ATC code	N05CM15 (WHO) ;
Identifiers
	IUPAC name 3-methylpent-1-yn-3-ol;
CAS Number	77-75-8 ;
PubChem CID	6494;
ChemSpider	21106516 ;
UNII	B017BC5B1N;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C6H10O
Molar mass	98.143 g/mol
3D model (JSmol)	Interactive image;
	SMILES CCC(C)(C#C)O;
	InChI InChI=1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3 ; Key:QXLPXWSKPNOQLE-UHFFFAOYSA-N ;
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Revision as of 19:41, 9 April 2015

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^[1] 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.^[2]^[3]^[4]^[5]

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

↑ DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen
↑ PMID 14903452 (PMID 14903452)
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↑ PMID 13028241 (PMID 13028241)
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↑ PMID 13159700 (PMID 13159700)
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↑ PMID 13783544 (PMID 13783544)
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Template:GABAAR PAMs

[1] DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen

[2] PMID 14903452 (PMID 14903452)
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[3] PMID 13028241 (PMID 13028241)
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[4] PMID 13159700 (PMID 13159700)
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[5] PMID 13783544 (PMID 13783544)
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[1]

[2]

[3]

[4]

[5]

@@ Line 1: / Line 1: @@
-{{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 -->
+<!--Pharmacokinetic data-->
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
+| bioavailability =
-| legal_US          =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
+| protein_bound =
-| legal_status      =
+| metabolism =
-| routes_of_administration =
+| 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
+| 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__
-'''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>
+{{SI}}
+{{CMG}}
-{{pharmacology-stub}}
+==Overview==
+'''Methylpentynol''' ('''Methylparafynol''', '''Dormison''', '''Atemorin''') is a [[Alcohol#tertiary|tertiary]] [[hexanol]] with [[hypnotic]]/[[sedative]] and [[anticonvulsant]] effects. 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 pmid | 14903452 }}</ref><ref>{{cite pmid | 13028241 }}</ref><ref>{{ cite pmid |     13159700 }}</ref><ref>{{ cite pmid | 13783544 }}</ref>
+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==
 {{reflist|2}}
 {{Hypnotics and sedatives}}
-{{WikiDoc Sources}}
+{{GABAAR PAMs}}
+[[Category:Tertiary alcohols]]
+[[Category:Anticonvulsants]]
+[[Category:Hexanols]]
+[[Category:GABAA receptor positive allosteric modulators]]
+[[Category:Drug]]

Methylpentynol: Difference between revisions

Revision as of 19:41, 9 April 2015

Overview

References

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