Viqualine

{{Short description|Medication}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 448239400

| IUPAC_name = 4-[3-[(3R,4R)-3-Ethenylpiperidin-4-yl]propyl]-6-methoxyquinoline

| image = Viqualine.png

| image_class = skin-invert-image

| width = 240

| tradename =

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| legal_status =

| routes_of_administration =

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 72714-74-0

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104497

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1Y3A5E2L1J

| PubChem = 3050111

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| ChemSpiderID = 2312222

| smiles = COC1=CC2=C(C=CN=C2C=C1)CCC[C@@H]3CCNC[C@@H]3C=C

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| StdInChI = 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

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| StdInChIKey = XFXANHWIBFMEOY-JKSUJKDBSA-N

| C=20 | H=26 | N=2 | O=1

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Viqualine (INN; developmental code PK-5078) is an antidepressant and anxiolytic drug that was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA602|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1–}}{{cite journal | vauthors = Faravelli C, Albanesi G, Sessarego A | title = Viqualine in resistant depression: a double-blind, placebo-controlled trial | journal = Neuropsychobiology | volume = 20 | issue = 2 | pages = 78–81 | year = 1988 | pmid = 3075725 | doi = 10.1159/000118477 }}{{cite book| vauthors = Papakostas GI, Fava M |title=Pharmacotherapy for Depression and Treatment-resistant Depression|url=https://books.google.com/books?id=zigp-66vq0MC&pg=PA304|year=2010|publisher=World Scientific|isbn=978-981-4287-59-3|pages=304–}} It acts as a potent and selective serotonin releasing agent (SRA) and serotonin reuptake inhibitor (SRI) similarly to para-chloroamphetamine (PCA).{{cite journal | vauthors = Le Fur G, Imbault F, Mitrani N, Marquis F, Renault C, Dubroeucq MC, Gueremy C, Uzan A | display-authors = 6 | title = The 5-hydroxytryptamine-releasing properties of two epimer quinoline derivatives | journal = Neuropharmacology | volume = 23 | issue = 2A | pages = 169–173 | date = February 1984 | pmid = 6717757 | doi = 10.1016/S0028-3908(84)80010-6 | s2cid = 30380886 }}{{cite journal | vauthors = Le Fur G, Imbault F, Mitrani N, Marquis F, Renault C, Dubroeucq MC, Gueremy C, Uzan A | title = The 5-hydroxytryptamine-releasing properties of two epimer quinoline derivatives | journal = Neuropharmacology | volume = 23 | issue = 2A | pages = 169–173 | date = February 1984 | pmid = 6717757 | doi = 10.1016/S0028-3908(84)80010-6| url = }} 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.{{cite journal | vauthors = Faravelli C, Albanesi G, Sessarego A | title = Viqualine in resistant depression: a double-blind, placebo-controlled trial | journal = Neuropsychobiology | volume = 20 | issue = 2 | pages = 78–81 | year = 1988 | pmid = 3075725 | doi = 10.1159/000118477 }} The drug has mainly been researched as a potential treatment for alcoholism.{{cite book | vauthors = Naranjo CA, Sellers EM | title = Recent Developments in Alcoholism | chapter = Serotonin Uptake Inhibitors Attenuate Ethanol Intake in Problem Drinkers | volume = 7 | pages = 255–266 | year = 1989 | pmid = 2522667 | doi = 10.1007/978-1-4899-1678-5_13 | isbn = 978-1-4899-1680-8 }}{{cite journal | vauthors = Naranjo CA, Sullivan JT, Kadlec KE, Woodley-Remus DV, Kennedy G, Sellers EM | title = Differential effects of viqualine on alcohol intake and other consummatory behaviors | journal = Clinical Pharmacology and Therapeutics | volume = 46 | issue = 3 | pages = 301–309 | date = September 1989 | pmid = 2673621 | doi = 10.1038/clpt.1989.142 | s2cid = 27080094 }}