Viqualine

Viqualine
Identifiers
	IUPAC name 4-[3-[(3R,4R)-3-Ethenylpiperidin-4-yl]propyl]-6-methoxyquinoline;
CAS Number	72714-74-0 ;
PubChem CID	3050111;
ChemSpider	2312222 ;
UNII	1Y3A5E2L1J;
ChEMBL	ChEMBL2104497 ;
CompTox Dashboard (EPA)	DTXSID601024516 ;
Chemical and physical data
Formula	C20H26N2O
Molar mass	310.441 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:XFXANHWIBFMEOY-JKSUJKDBSA-N ;
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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 (SRA) and serotonin reuptake inhibitor (SRI) similarly to para-chloroamphetamine (PCA).^[3]^[4]^[5] In addition, viqualine displaces diazepam from the GABA_A receptor and produces benzodiazepine-like effects, indicating that it is also a positive allosteric modulator of the benzodiazepine site of the GABA_A receptor.^[3]^[6] The drug has mainly been researched as a potential treatment for alcoholism.^[7]^[8]

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[1]
Elks J (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]
Papakostas GI, Fava M (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, et al. (February 1984). "The 5-hydroxytryptamine-releasing properties of two epimer quinoline derivatives". Neuropharmacology. 23 (2A): 169–173. doi:10.1016/S0028-3908(84)80010-6. PMID 6717757. S2CID 30380886.
[5]
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): 169–173. PMID 6717757.
[6]
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.
[7]
Naranjo CA, Sellers EM (1989). "Serotonin Uptake Inhibitors Attenuate Ethanol Intake in Problem Drinkers". Recent Developments in Alcoholism. Vol. 7. pp. 255–266. doi:10.1007/978-1-4899-1678-5_13. ISBN 978-1-4899-1680-8. PMID 2522667.
[8]
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): 301–309. doi:10.1038/clpt.1989.142. PMID 2673621. S2CID 27080094.

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[Elks2014-1] [1]
Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1–. ISBN 978-1-4757-2085-3.

[pmid3075725-2] [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.

[PapakostasFava2010-3] [3]
Papakostas GI, Fava M (2010). Pharmacotherapy for Depression and Treatment-resistant Depression. World Scientific. pp. 304–. ISBN 978-981-4287-59-3.

[pmid6717757-4] [4]
Le Fur G, Imbault F, Mitrani N, Marquis F, Renault C, Dubroeucq MC, et al. (February 1984). "The 5-hydroxytryptamine-releasing properties of two epimer quinoline derivatives". Neuropharmacology. 23 (2A): 169–173. doi:10.1016/S0028-3908(84)80010-6. PMID 6717757. S2CID 30380886.

[LeFurImbaultMitraniMarquis1984-5] [5]
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): 169–173. PMID 6717757.

[FaravelliAlbanesi1988-6] [6]
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.

[pmid2522667-7] [7]
Naranjo CA, Sellers EM (1989). "Serotonin Uptake Inhibitors Attenuate Ethanol Intake in Problem Drinkers". Recent Developments in Alcoholism. Vol. 7. pp. 255–266. doi:10.1007/978-1-4899-1678-5_13. ISBN 978-1-4899-1680-8. PMID 2522667.

[pmid2673621-8] [8]
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): 301–309. doi:10.1038/clpt.1989.142. PMID 2673621. S2CID 27080094.

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Viqualine

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References

Identifiers

IUPAC name 4-[3-[(3R,4R)-3-Ethenylpiperidin-4-yl]propyl]-6-methoxyquinoline
CAS Number	72714-74-0^Y
PubChem CID	3050111
ChemSpider	2312222^N
UNII	1Y3A5E2L1J
ChEMBL	ChEMBL2104497^N
CompTox Dashboard (EPA)	DTXSID601024516
Chemical and physical data
Formula	C₂₀H₂₆N₂O
Molar mass	310.441 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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