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hexacyclonate sodium

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hexacyclonate sodium

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Hexacyclonate (Gevilon) is a stimulant drug. It has been used for the treatment of alcoholism and for increasing motivation in elderly patients, but Gevilon (containing a different active substance - gemfibrozil) is now mainly used for the treatment of hyperlipoproteinaemia. It is chemically similar to the anticonvulsant gabapentin, with a hydroxyl group replacing the amine.

Chemical data

Formula
C9H15NaO3
Molecular weight
194.2 g/mol
IUPAC name
sodium 2-[1-(hydroxymethyl)cyclohexyl]acetate
SMILES
C1CCC(CC1)(CC(=O)[O-])CO.[Na+]
InChIKey
YPKROQTVZNJPNX-UHFFFAOYSA-M
Polar surface area
60.4 Ų
H-bond donors
1
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 2
Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
194.092
Show 2 more facts
canonical SMILES
C1CCC(CC1)(CC(=O)[O-])CO.[Na+]
chemical formula
C₉H₁₅NaO₃
Sources (1)

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Encyclopedic overview

2 sections
Contents
  • Synthesis
  • References

Hexacyclonate (Gevilon) is a stimulant drug. It has been used for the treatment of alcoholism and for increasing motivation in elderly patients, but Gevilon (containing a different active substance - gemfibrozil) is now mainly used for the treatment of hyperlipoproteinaemia. 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== center|500px 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). == References ==

Excerpted from Wikipedia’s “hexacyclonate sodium” article, available under the CC BY-SA 4.0 licence.

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