Methylpentynol Explained

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^[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]}

The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative.^[5] 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 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

• Clocental^[7]
• Ethchlorvynol

Notes and References

1. DE . patent . 289800 . 1913-11-30 . Bayer, Leverkusen . Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen .
2. Hirsh HL, Orsinger WH . Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity . American Practitioner and Digest of Treatment . 3 . 1 . 23–6 . January 1952 . 14903452 .
3. Schaffarzick RW, Brown BJ . The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols . Science . 116 . 3024 . 663–5 . December 1952 . 13028241 . 10.1126/science.116.3024.663 . 1952Sci...116..663S .
4. Herz A . [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 . March 1954 . 13159700 .
5. Weaver LC, Alexander WM, Abreu BE . Anticonvulsant activity of compounds related to methylparafynol . Archives Internationales de Pharmacodynamie et de Therapie . 131 . 116–22 . April 1961 . 13783544 .
6. Book: Hines, Richard Devenport . vanc . The Pursuit of Oblivion . 2002 . 327 .
7. Grimene W, Emde H . DE . 959485 . 1957 .