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Methylpentynol

Methylpentynol
Structural formula
Space-filling model of methylpentynol
Clinical data
Trade namesOblivon
Routes of
administration
oral
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.000.960 Edit this at Wikidata
Chemical and physical data
FormulaC6H10O
Molar mass98.143 g/mol g·mol−1
3D model (JSmol)
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Methylpentynol (Methylparafynol, Dormison, Atemorin, Oblivon) is a tertiary hexanol with hypnotic/sedative and anticonvulsant effects and an exceptionally low therapeutic index. 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]

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

Synthesis

Methylpentynol is prepared by reaction of butanone (MEK) with sodium acetylide. This reaction must be done in anhydrous conditions and in an inert atmosphere.

See also

References

  1. ^ DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen 
  2. ^ Hirsh, H. L.; Orsinger, W. H. (1952). "Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity". American practitioner and digest of treatment. 3 (1): 23–26. PMID 14903452.
  3. ^ Schaffarzick, R. W.; Brown, B. J. (1952). "The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols". Science. 116 (3024): 663–665. doi:10.1126/science.116.3024.663. PMID 13028241.
  4. ^ Herz, A. (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): 198–199. PMID 13159700.
  5. ^ Weaver, L. C.; Alexander, W. M.; Abreu, B. E. (1961). "Anticonvulsant activity of compounds related to methylparafynol". Archives Internationales de Pharmacodynamie et de Thérapie. 131: 116–122. PMID 13783544.
  6. ^ Richard Devenport Hines, The Pursuit of Oblivion (2002) pp 327
  7. ^ W. Grimene and H. Emde, German Patent 959,485 (1957).