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Methylpentynol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Methylpentynol
Structural formula
Space-filling model of methylpentynol
Clinical data
Trade namesOblivon
Other namesMethylparafynol
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Identifiers
  • 3-methylpent-1-yn-3-ol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.000.960Edit this at Wikidata
Chemical and physical data
FormulaC6H10O
Molar mass98.145 g·mol−1
3D model (JSmol)
  • CCC(C)(C#C)O
  • InChI=1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3 ☒N
  • Key:QXLPXWSKPNOQLE-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Methylpentynol (also known asmethylparafynol, trade namesDormison,Atemorin,Oblivon) is atertiary pentynol withhypnotic/sedative andanticonvulsant effects and an exceptionally lowtherapeutic index. It was discovered byBayer in 1913[2] and was used shortly thereafter for the treatment ofinsomnia, but its use was quickly phased out in response to newer drugs with far more favorable safety profiles.[3][4][5]

The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative.[6] The drug was quickly overshadowed at that point bybenzodiazepines and is no longer sold anywhere.[7]

Synthesis

[edit]

Methylpentynol is prepared by reaction ofbutanone (MEK) with sodiumacetylide in liquidammonia. This reaction must be done in anhydrous conditions and in an inert atmosphere.

Applications

[edit]

As building block in the synthesis of:

  1. Phthalofyne (1,2-Benzenedicarboxylic acid, mono(1-ethyl-1-methyl-2-propynyl) ester) [131-67-9]
  2. Anansiol (1-ethyl-1-methylprop-2-ynyl carbamate) [302-66-9]
  3. Bason ( 2-Bromoethynyl-2-butanol) [2028-52-6]

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  2. ^DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen 
  3. ^Hirsh HL, Orsinger WH (January 1952). "Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity".American Practitioner and Digest of Treatment.3 (1):23–6.PMID 14903452.
  4. ^Schaffarzick RW, Brown BJ (December 1952). "The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols".Science.116 (3024):663–5.Bibcode:1952Sci...116..663S.doi:10.1126/science.116.3024.663.PMID 13028241.
  5. ^Herz A (March 1954). "[A new type of hypnotic; unsaturated tertiary carbinols; experimental studies on therapeutic use of 3-methyl-pentin-ol-3 (methylparafynol)]".Arzneimittel-Forschung.4 (3):198–9.PMID 13159700.
  6. ^Weaver LC, Alexander WM, Abreu BE (April 1961). "Anticonvulsant activity of compounds related to methylparafynol".Archives Internationales de Pharmacodynamie et de Therapie.131:116–22.PMID 13783544.
  7. ^Hines RD (2002).The Pursuit of Oblivion. p. 327.
  8. ^DE 959485, Grimene W, Emde H, issued 1957 
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