Pipequaline - CAS 77472-98-1
Catalog number: 77472-98-1
Category: Inhibitor
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Molecular Formula:
Molecular Weight:
GABA Receptor
Pipequaline is a non-selective GABAA receptor partial agonist that is potentially used as an anxiolytic drug of the nonbenzodiazepine class. It exhibits anxiolytic properties and very little sedative, amnestic or anticonvulsant effects. Currently pipequaline is only used for research.
Brife Description:
non-selective GABAA receptor partial agonist, anxiolytic
Solid powder
Pipequalinum; Pipequalina; UNII-J3S205V4I2; PK-8165; 2-phenyl-4-(2-piperidin-4-ylethyl)quinoline
Soluble in DMSO.
Store in a cool and dry place and at 0-4 ℃ for short term (days to weeks) or -66 ℃ for long term (months to years).
Pipequaline is a non-selective GABAA receptor partial agonist.
Shelf Life:
2 years
Boiling Point:
489.2ºC at 760 mmHg
Canonical SMILES:
1.Differential effects of 4'-chlorodiazepam on expressed human GABAA receptors.
Lan NC1, Chen JS, Johnson D, Gee KW. J Neurochem. 1995 Feb;64(2):684-8.
The interactions of the atypical benzodiazepine 4'-chlorodiazepam (Ro 5-4864) with functionally expressed human GABAA receptor cDNAs were determined. Cotransfection of human alpha 2, beta 1, and gamma 2 subunits was capable of reconstituting a 4'-chlorodiazepam recognition site as revealed by a dose-dependent potentiation of t-[35S]butylbicyclophosphorothionate ([35S]-TBPS) binding to the GABA-activated chloride channel. This site is found on GABAA receptor complexes containing sites for GABA agonist-like benzodiazepines and neuroactive steroids. The importance of the alpha subunit was further demonstrated as substitution of either alpha 1 or alpha 3 for the alpha 2 subunit did not reconstitute a 4'-chlorodiazepam recognition site that was capable of modulating [35S]TBPS binding under the same experimental conditions. The 4'-chlorodiazepam modulatory site was shown to be distinct from the benzodiazepine site, but the phenylquinolines PK 8165 and PK 9084 produced effects similar to 4'-chlorodiazepam, consistent with the previous analysis of the 4'-chlorodiazepam site in brain homogenates.
2.Pipequaline transport from blood to brain and liver: role of plasma protein-bound drug.
Essassi D1, Urien S, Zini R, Tillement JP. J Pharm Pharmacol. 1989 Sep;41(9):595-600.
Brain uptake of pipequaline (45319 RP) has been studied in-vivo after a single capillary transit by intracarotid injection to rats. Pipequaline is extensively bound to plasma proteins: i.e. human serum albumin (HSA), alpha-1-acid glycoprotein (AAG), lipoproteins and blood cells, mainly erythrocytes. The dialysable drug fraction as measured in-vitro by equilibrium dialysis at 37 degrees C, was inversely related to the concentration of binding component. Similarly, the brain uptake of pipequaline was inversely related to the protein concentration of the injected solution. However, the measured brain uptake of pipequaline was higher than those predicted by in-vitro measurements of dialysable drug for all proteins and erythrocytes, except HSA. These results show that a fraction of bound pipequaline as measured in-vitro is available for transport through the blood brain barrier. HSA-bound pipequaline is an exception as it is restricted to the vascular space.
3.Binding in vitro of pipequaline (45319 RP) onto plasma proteins and blood cells in man.
Essassi D1, Zini R, Hamberger C, Urien S, Rougeot C, Uzan A, Tillement JP. Biochem Pharmacol. 1987 Oct 15;36(20):3501-7.
Serum binding of pipequaline, a new anxiolytic drug, was studied in vitro by equilibrium dialysis. The percent binding in serum is high, 96.3%, and remains constant within the range of therapeutic concentrations. Investigations performed on isolated proteins with a wide range of concentrations showed one site with a high affinity constant (Ka = 450,000 M-1) for alpha 1-acid glycoprotein and two sites with a lower affinity constant (Ka = 58,000 M-1) for human serum albumin. Binding to lipoproteins was saturable, with an affinity constant of 22,000 less than or equal to Ka less than or equal to 35,000 M-1. Over the range of therapeutic concentrations, the ratio of pipequaline concentrations in serum and red blood cells remained constant (14.4%) and was shown to be dependent on the free fraction of pipequaline in serum.
4.Phenylquinolines PK 8165 and PK 9084 allosterically modulate [35S]t-butylbicyclophosphorothionate binding to a chloride ionophore in rat brain via a novel Ro5 4864 binding site.
Gee KW. J Pharmacol Exp Ther. 1987 Mar;240(3):747-53.
The binding of the cage convulsant, [35S]t-butylbicyclophosphorothionate ([35S]TBPS), to a picrotoxin-sensitive site in rat cerebral cortical homogenates was used to identify and characterize the site of action of the phenylquinolines PK 8165 and PK 9084, the isoquinoline PK 11195 and the atypical benzodiazepine (BZ) Ro5 4864. These agents were found to allosterically modulate the binding of 2 nM [35S]TBPS in a pharmacologically relevant fashion. Evidence is presented to suggest that these compounds share a common site of action as modulators of [35S]TBPS binding. The relative potencies of these compounds in vitro are in the submicromolar to micromolar concentration range and correlate well with the concentrations reported to elicit specific responses in behavioral and electrophysiologic studies. Modulation of [35S]TBPS binding in vitro is affected by micromolar quantities of gamma-aminobutyric acid in a (+)-bicuculline-sensitive fashion and is unaffected by the central BZ receptor "antagonist" Ro15 1788.
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CAS 77472-98-1 Pipequaline

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