Hexacyclonate (Gevilon) is a stimulant drug. It has been used for the treatment of alcoholism[1] and for increasing motivation in elderly patients,[2] but Gevilon (containing a different active substance - gemfibrozil) is now mainly used for the treatment of hyperlipoproteinaemia.[3][4] It is chemically similar to the anticonvulsant gabapentin, with a hydroxyl group replacing the amine.
The latter use may be incorrectly assigned, as "Gevilon" has been used as a trade name for gemfibrozil, a well-known drug for dislipidemia.
Synthesis
The treatment of 1,1-Cyclohexanediacetic acid [4355-11-7] (1) with acetic anhydride led to Cyclohexanediacetic anhydride [1010-26-0] (2). Esterification with methanol led to 1,1-Cyclohexanediacetic acid mono methyl ester [60142-94-1] (3). Treatment of the monoacid with potassium hydroxide gave the alkoxide (4). Treatment with bromine in the presence of tetrachloromethane gave Methyl 3,3-pentamethylene-4-bromobutyrate (5). Reaction with aqueous lye gave 2-Oxaspiro[4.5]decan-3-one (GO 177) [7236-78-4] (6). Further treatment with aqueous lye completed the synthesis of hexacyclonate (7).[5]
References
↑"Adjunctive treatment of the chronic alcoholic with hexacyclonate sodium". The Illinois Medical Journal121: 546–8. May 1962. PMID13878809.
↑"Pharmaco-motivation of the geriatric patient: a preliminary report on hexacyclonate". The Journal of the Louisiana State Medical Society114: 23–6. January 1962. PMID14476295.
↑"Therapeutic effect of gevilon in patients with hyperlipoproteinaemia". Materia Medica Polona. Polish Journal of Medicine and Pharmacy24 (2): 91–5. 1992. PMID1307777.
↑"Pharmacoeconomic aspects of patients treated by hemodialysis". Bratislavske Lekarske Listy104 (10): 329–34. 2003. PMID15055734.
↑Robert I Meltzer, Jr John Shavel, Vigelius Wolf-Dieter, U.S. Patent 3,007,940 (1961 to Warner Lambert Pharmaceutical).
