Methylpentynol

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]

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  • Withdrawn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
Chemical and physical data
FormulaC6H10O
Molar mass98.143 g/mol g·mol−1
3D model (JSmol)
 NY (what is this?)  (verify)

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).


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