Hexacyclonate

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 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

1. Chesrow EJ, Sabatini R, Musci JP, Kaplitz SE, Marquardt GH (May 1962). "Adjunctive treatment of the chronic alcoholic with hexacyclonate sodium". The Illinois Medical Journal. 121: 546–8. PMID   13878809.
2. Morrison BO (January 1962). "Pharmaco-motivation of the geriatric patient: a preliminary report on hexacyclonate". The Journal of the Louisiana State Medical Society. 114: 23–6. PMID   14476295.
3. Milewicz A, Plamieniak Z, Bohdanowicz-Pawlak A (1992). "Therapeutic effect of gevilon in patients with hyperlipoproteinaemia". Materia Medica Polona. Polish Journal of Medicine and Pharmacy. 24 (2): 91–5. PMID   1307777.
4. Gazdikova K, Korecka P, Springer V, Gazdik F (2003). "Pharmacoeconomic aspects of patients treated by hemodialysis". Bratislavske Lekarske Listy. 104 (10): 329–34. PMID   15055734.
5. Robert I Meltzer, Jr John Shavel, Vigelius Wolf-Dieter, U.S. patent 3,007,940 (1961 to Warner Lambert Pharmaceutical).