Methylpentynol

Chemical compound From Wikipedia, the free encyclopedia

Methylpentynol (also known as methylparafynol, trade names Dormison, Atemorin, Oblivon) is a tertiary pentynol with hypnotic/sedative and anticonvulsant effects and an exceptionally low therapeutic index. It was discovered by Bayer in 1913[2] 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.[3][4][5]

Trade namesOblivon
Other namesMethylparafynol
Routes of
administrationBy mouth
ATC code
Quick facts Clinical data, Trade names ...
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
  • BR: Class C1 (Other controlled substances)[1]
  • Withdrawn
Identifiers
  • 3-methylpent-1-yn-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.000.960 Edit 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)
Close

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 by benzodiazepines and is no longer sold anywhere.[7]

Synthesis

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

Applications

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

References

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