Methylpentynol (Methylparafynol, Dormison, Atemorin) is a tertiaryhexanol with hypnotic/sedative and anticonvulsant effects. It was discovered by Bayer in 1913 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.
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).
^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 treatment3 (1): 23–26. PMID14903452.edit
^Herz, A. (1954). "A new type of hypnotic; unsaturated tertiary carbinols; experimental studies on therapeutic use of 3-methyl-pentin-ol-3 (methylparafynol)". Arzneimittel-Forschung4 (3): 198–199. PMID13159700.edit
^Weaver, L. C.; Alexander, W. M.; Abreu, B. E. (1961). "Anticonvulsant activity of compounds related to methylparafynol". Archives internationales de pharmacodynamie et de therapie131: 116–122. PMID13783544.edit