Hexacyclonate

Identifiers
IUPAC name [1-(hydroxymethyl)cyclohexyl]acetic acid
CAS Number	7491-42-1
PubChem CID	23444
ChemSpider	21921 Y
UNII	2K0FP9UB6A
ChEMBL	ChEMBL2110826
CompTox Dashboard (EPA)	DTXSID30225885 DTXSID60220363, DTXSID30225885
Chemical and physical data
Formula	C9H16O3
Molar mass	172.224 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(O)CC1(CO)CCCCC1
InChI InChI=1S/C9H16O3/c10-7-9(6-8(11)12)4-2-1-3-5-9/h10H,1-7H2,(H,11,12) Y Key:WMJPAYUKEVEBCN-UHFFFAOYSA-N Y
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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.

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]

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