Methylpentynol
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| Clinical data | |
|---|---|
| Trade names | Oblivon |
| ATC code | N05CM15 (WHO) |
| Identifiers | |
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| CAS Number |
77-75-8  |
| PubChem (CID) | 6494 |
| ChemSpider |
21106516  |
| UNII |
B017BC5B1N |
| ECHA InfoCard | 100.000.960 |
| Chemical and physical data | |
| Formula | C6H10O |
| Molar mass | 98.143 g/mol |
| 3D model (Jmol) | Interactive image |
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| (what is this?) (verify) | |
Methylpentynol (Methylparafynol, Dormison, Atemorin, Oblivon) is a tertiary hexanol with hypnotic/sedative and anticonvulsant effects. 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; it was overshadowed at that point by benzodiazepines and the continued popularity of non-barbiturate sedatives such as meprobamate. [6]
Synthesis
Methylpentynol is prepared by reaction of butanone with sodium acetylide.
See also
References
- ↑ DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen
- ↑ Hirsh, H. L.; Orsinger, W. H. (1952). "Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity". American practitioner and digest of treatment. 3 (1): 23–26. PMID 14903452.
- ↑ Schaffarzick, R. W.; Brown, B. J. (1952). "The anticonvulsant activity and toxicity of methylparafynol (dormison) and some other alcohols". Science. 116 (3024): 663–665. doi:10.1126/science.116.3024.663. PMID 13028241.
- ↑ Herz, A. (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): 198–199. PMID 13159700.
- ↑ Weaver, L. C.; Alexander, W. M.; Abreu, B. E. (1961). "Anticonvulsant activity of compounds related to methylparafynol". Archives Internationales de Pharmacodynamie et de Thérapie. 131: 116–122. PMID 13783544.
- ↑ Richard Devenport Hines, The Pursuit of Oblivion (2002) pp 327
- ↑ W. Grimene and H. Emde, German Patent 959,485 (1957).
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