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Hexacyclonate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Hexacyclonate
Identifiers
  • [1-(hydroxymethyl)cyclohexyl]acetic acid
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC9H16O3
Molar mass172.224 g·mol−1
3D model (JSmol)
  • O=C(O)CC1(CO)CCCCC1
  • InChI=1S/C9H16O3/c10-7-9(6-8(11)12)4-2-1-3-5-9/h10H,1-7H2,(H,11,12) checkY
  • Key:WMJPAYUKEVEBCN-UHFFFAOYSA-N checkY
  (verify)

Hexacyclonate (Gevilon) is astimulant drug. It has been used for the treatment ofalcoholism[1] and for increasing motivation in elderly patients,[2] but Gevilon (containing a different active substance -gemfibrozil) is now mainly used for the treatment ofhyperlipoproteinaemia.[3][4] It is chemically similar to the anticonvulsantgabapentin, with a hydroxyl group replacing the amine.

The latter use may be incorrectly assigned, as "Gevilon" has been used as a trade name forgemfibrozil, a well-known drug for dislipidemia.

Synthesis

[edit]

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

[edit]
  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).
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