Methylpentynol

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Methylpentynol
Structural formula
Space-filling model of methylpentynol
Clinical data
Trade names Oblivon
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.000.960
Chemical and physical data
Formula C6H10O
Molar mass 98.143 g/mol
3D model (Jmol)
 NYesY (what is this?)  (verify)

Methylpentynol (Methylparafynol, Dormison, Atemorin, Oblivon) 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]

The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative; it was overshadowed at that point by benzodiazepines and the continued popularity of non-barbiturate sedatives such as meprobamate. [6]

Synthesis[edit]

Methylpentynol is prepared by reaction of butanone with sodium acetylide.

See also[edit]

References[edit]

  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).