Methylpentynol (Methylparafynol, 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]
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.
^DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen
^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.
PMID14903452.
^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.
PMID13159700.
^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.
PMID13783544.
^Hines RD (2002). The Pursuit of Oblivion. p. 327.