Structure via PubChem · Public domain (PubChem)
hexacyclonate sodium
Sign in to saveHexacyclonate (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)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- 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.