Methylpentynol

Methylpentynol
Structural formula
Space-filling model of methylpentynol
Clinical data
Trade namesOblivon
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
IUPAC name
  • 3-methylpent-1-yn-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.000.960
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Chemical and physical data
FormulaC6H10O
Molar mass98.145 g·mol−1
3D model (JSmol)
SMILES
  • CCC(C)(C#C)O
InChI
  • 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 (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 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ Hines RD (2002). The Pursuit of Oblivion. p. 327.
  7. ↑ DE 959485, Grimene W, Emde H, issued 1957
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