Hexacyclonate
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| _other_data=[1-(hydroxymethyl)cyclohexyl]acetic acid
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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 dislypidemia.
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
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- ↑ Robert I Meltzer, Jr John Shavel, Vigelius Wolf-Dieter, U.S. patent 3007940 (1961 to Warner Lambert Pharmaceutical).
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