Chemistry:Methylpentynol
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| Trade names | Oblivon |
| Routes of administration | By mouth |
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| Formula | C6H10O |
| Molar mass | 98.145 g·mol−1 |
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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:
- Phthalofyne (1,2-Benzenedicarboxylic acid, mono(1-ethyl-1-methyl-2-propynyl) ester) [131-67-9]
- Anansiol (1-ethyl-1-methylprop-2-ynyl carbamate) [302-66-9]
- Bason ( 2-Bromoethynyl-2-butanol) [2028-52-6]
See also
References
- ↑ "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen" DE patent 289800, issued 1913-11-30, assigned to Bayer, Leverkusen
- ↑ "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. PMID 14903452.
- ↑ "The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols". Science 116 (3024): 663–5. December 1952. doi:10.1126/science.116.3024.663. PMID 13028241. Bibcode: 1952Sci...116..663S.
- ↑ "[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. PMID 13159700.
- ↑ "Anticonvulsant activity of compounds related to methylparafynol". Archives Internationales de Pharmacodynamie et de Therapie 131: 116–22. April 1961. PMID 13783544.
- ↑ Hines, Richard Devenport (2002). The Pursuit of Oblivion. pp. 327.
- ↑ Grimene W, Emde H, DE patent 959485, issued 1957
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