Pipequaline

Pipequaline

Systematic (IUPAC) name
2-phenyl-4-(2-piperidin-4-ylethyl)quinoline
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	77472-98-1
ATC code	None
PubChem	CID 71219
ChemSpider	64354 Y
UNII	J3S205V4I2 Y
Chemical data
Formula	C22H24N2
Mol. mass	316.439 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C22H24N2/c1-2-6-18(7-3-1)22-16-19(11-10-17-12-14-23-15-13-17)20-8-4-5-9-21(20)24-22/h1-9,16-17,23H,10-15H2 Y Key:AMEWZCMTSIONOX-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

Pipequaline (PK-8165) is an anxiolytic drug with a novel chemical structure that is not closely related to other drugs of this type. It has a similar pharmacological profile to the benzodiazepine family of drugs, but with mainly anxiolytic properties and very little sedative, amnestic or anticonvulsant effects, and so is classified as a nonbenzodiazepine anxiolytic.^[1][2][3]

Pipequaline acts as a non-selective GABA_A receptor partial agonist.^[4][5][6] While its profile of anxiolytic effects without sedation would appear to have potential medical applications, pipequaline has never been developed for medical use and is currently only used in scientific research.

References

1. ^ von Frenckell R, Ansseau M, Bonnet D. Evaluation of the sedative properties of PK 8165 (pipequaline), a benzodiazepine partial agonist, in normal subjects. International Clinical Psychopharmacology. 1986 Jan;1(1):24-35.
2. ^ Willer JC, Von Frenkell R, Bonnet D, Le Fur G. The ability of PK 8165, a quinoline derivative, to reduce responses to a stressful situation in a double-blind study in man. Neuropharmacology. 1986 Mar;25(3):275-81.
3. ^ Eves FF, Curran HV, Shine P, Lader MH. The effects on memory of pipequaline, alone or in combination with diazepam. Psychopharmacology (Berlin). 1988;95(3):386-9.
4. ^ Mizoule J, Rataud J, Uzan A, Mazadier M, Daniel M, Gauthier A, Ollat C, Gueremy C, Renault C, Dubroeucq MC, et al. Pharmacological evidence that PK 8165 behaves as a partial agonist of brain type benzodiazepine receptors. Archives Internationales de Pharmacodynamie et de Therapie. 1984 Oct;271(2):189-97.
5. ^ Benavides J, Malgouris C, Flamier A, Tur C, Quarteronet D, Begassat F, Camelin JC, Uzan A, Gueremy C, Le Fur G. Biochemical evidence that 2-phenyl-4[(4-piperidinyl) ethyl]quinoline, a quinoline derivative with pure anticonflict properties, is a partial agonist of benzodiazepine receptors. Neuropharmacology. 1984 Oct;23(10):1129-36.
6. ^ Debonnel G, de Montigny C. Pipequaline acts as a partial agonist of benzodiazepine receptors: an electrophysiological study in the hippocampus of the rat. Neuropharmacology. 1987 Sep;26(9):1337-42.