Viqualine

Viqualine (INN) (developmental code name PK-5078) is an antidepressant and anxiolytic drug that was never marketed.[1][2][3] It acts as a potent and selective serotonin releasing agent and serotonin reuptake inhibitor.[3][4] In addition, viqualine displaces diazepam from the GABAA receptor and produces benzodiazepine-like effects, indicating that it is also a positive allosteric modulator of the benzodiazepine site of the GABAA receptor.[3][5] The drug has mainly been researched as a potential treatment for alcoholism.[6][7]

Viqualine
Identifiers
IUPAC name
  • 4-[3-[(3R,4R)-3-Ethenylpiperidin-4-yl]propyl]-6-methoxyquinoline
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H26N2O
Molar mass310.441 g·mol−1
3D model (JSmol)
SMILES
  • COC1=CC2=C(C=CN=C2C=C1)CCC[C@@H]3CCNC[C@@H]3C=C
InChI
  • InChI=1S/C20H26N2O/c1-3-15-14-21-11-9-16(15)5-4-6-17-10-12-22-20-8-7-18(23-2)13-19(17)20/h3,7-8,10,12-13,15-16,21H,1,4-6,9,11,14H2,2H3/t15-,16+/m0/s1 N
  • Key:XFXANHWIBFMEOY-JKSUJKDBSA-N N
 NY (what is this?)  (verify)

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1–. ISBN 978-1-4757-2085-3.
  2. Faravelli C, Albanesi G, Sessarego A (1988). "Viqualine in resistant depression: a double-blind, placebo-controlled trial". Neuropsychobiology. 20 (2): 78–81. doi:10.1159/000118477. PMID 3075725.
  3. George I. Papakostas; Maurizio Fava (2010). Pharmacotherapy for Depression and Treatment-resistant Depression. World Scientific. pp. 304–. ISBN 978-981-4287-59-3.
  4. Le Fur G, Imbault F, Mitrani N, Marquis F, Renault C, Dubroeucq MC, Gueremy C, Uzan A (February 1984). "The 5-hydroxytryptamine-releasing properties of two epimer quinoline derivatives". Neuropharmacology. 23 (2A): 169–73. doi:10.1016/S0028-3908(84)80010-6. PMID 6717757. S2CID 30380886.
  5. Faravelli, Carlo; Albanesi, Giorgio; Sessarego, Antonella (1988). "Viqualine in Resistant Depression: A Double-Blind, Placebo-Controlled Trial". Neuropsychobiology. 20 (2): 78–81. doi:10.1159/000118477. ISSN 1423-0224. PMID 3075725.
  6. Naranjo CA, Sellers EM (1989). "Serotonin uptake inhibitors attenuate ethanol intake in problem drinkers". Recent Developments in Alcoholism. 7: 255–66. doi:10.1007/978-1-4899-1678-5_13. ISBN 978-1-4899-1680-8. PMID 2522667.
  7. Naranjo CA, Sullivan JT, Kadlec KE, Woodley-Remus DV, Kennedy G, Sellers EM (September 1989). "Differential effects of viqualine on alcohol intake and other consummatory behaviors". Clinical Pharmacology and Therapeutics. 46 (3): 301–9. doi:10.1038/clpt.1989.142. PMID 2673621. S2CID 27080094.


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