Methylpentynol

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Methylpentynol
Meparfynol.svg
Systematic (IUPAC) name
3-methylpent-1-yn-3-ol
Clinical data
Legal status
?
Identifiers
CAS number 77-75-8 YesY
ATC code N05CM15
PubChem CID 6494
ChemSpider 21106516 N
UNII B017BC5B1N YesY
Chemical data
Formula C6H10O 
Mol. mass 98.143 g/mol
 N (what is this?)  (verify)

Methylpentynol (Methylparafynol, Dormison, Atemorin) 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]

See also[edit]

To make meparfynol proper, the alcohol must be reacted with phosgene followed by ammonia to form the carbamate (see patent). Also, ethynylation of cyclohexanone is one of the preferred analogs (c.f. Lednicer book 1).

References[edit]

  1. ^ DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen 
  2. ^ 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.  edit
  3. ^ 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.  edit
  4. ^ 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.  edit
  5. ^ Weaver, L. C.; Alexander, W. M.; Abreu, B. E. (1961). "Anticonvulsant activity of compounds related to methylparafynol". Archives internationales de pharmacodynamie et de therapie 131: 116–122. PMID 13783544.  edit
  6. ^ K. Junkmann and H. Pfeiffer, U.S. Patent 2,816,910 (1957).
  7. ^ W. Grimene and H. Emde, German Patent 959,485 (1957).