Pipequaline HCl
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MedKoo CAT#: 329522

CAS#: 80221-58-5 (HCl)

Description: Pipequaline, also known as PK-8165, is an anxiolytic drug that was never marketed. It possesses a novel chemical structure that is not closely related to other drugs of this type. The drug 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. Pipequaline acts as a non-selective GABAA receptor partial agonist. 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.

Chemical Structure

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Pipequaline HCl
CAS# 80221-58-5 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329522
Name: Pipequaline HCl
CAS#: 80221-58-5 (HCl)
Chemical Formula: C22H25ClN2
Exact Mass: 316.19
Molecular Weight: 352.906
Elemental Analysis: C, 74.88; H, 7.14; Cl, 10.05; N, 7.94

Price and Availability

Size Price Availability Quantity
100mg USD 350
200mg USD 650
500mg USD 1450
1g USD 1950
2g USD 3450
5g USD 5850
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Related CAS #: 80221-58-5 (HCl)   77472-98-1 (free base)  

Synonym: Pipequaline; PK 8165; PK-8165; PK8165; Pipequaline HCl; Pipequaline hydrochloride

IUPAC/Chemical Name: 2-Phenyl-4-(2-(4-piperidinyl)ethyl)quinoline monohydrochloride

InChi Key: JWEMPGHGMSUJIS-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H24N2.ClH/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;1H

SMILES Code: [H]Cl.C1(C2=CC=CC=C2)=NC3=CC=CC=C3C(CCC4CCNCC4)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Pipequaline hydrochloride (PK-8165 hydrochloride) is a partial benzodiazepine receptor agonist with anxiolytic activity.
In vitro activity: TBD
In vivo activity: PK 8165, a ligand of BZD receptors, is an anxiolytic devoid of sedative and anticonvulsant effects. PK 8165, applied microiontophoretically or administered i.v. at low doses, suppressed CCK-8S-induced activation of rat hippocampal pyramidal neurons, whereas, at high doses it antagonized the effect of microiontophoretic applications of flurazepam. These results indicate that PK 8165 acts as a mixed agonist-antagonist at BZD receptors and suggest that the suppression of CCK-8S-induced activation by BZD might be related to their anxiolytic property rather than to their sedative or anticonvulsant activity. Reference: Eur J Pharmacol. 1985 Jun 19;112(3):415-8. https://pubmed.ncbi.nlm.nih.gov/2990972/

Preparing Stock Solutions

The following data is based on the product molecular weight 352.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. 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. doi: 10.1016/0028-3908(87)90096-7. PMID: 2823163. 2. Bradwejn J, De Montigny C. Effects of PK 8165, a partial benzodiazepine receptor agonist, on cholecystokinin-induced activation of hippocampal pyramidal neurons: a microiontophoretic study in the rat. Eur J Pharmacol. 1985 Jun 19;112(3):415-8. doi: 10.1016/0014-2999(85)90790-3. PMID: 2990972.
In vitro protocol: TBD
In vivo protocol: 1. 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. doi: 10.1016/0028-3908(87)90096-7. PMID: 2823163. 2. Bradwejn J, De Montigny C. Effects of PK 8165, a partial benzodiazepine receptor agonist, on cholecystokinin-induced activation of hippocampal pyramidal neurons: a microiontophoretic study in the rat. Eur J Pharmacol. 1985 Jun 19;112(3):415-8. doi: 10.1016/0014-2999(85)90790-3. PMID: 2990972.

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1: Eves FF, Curran HV, Shine P, Lader MH. The effects on memory of pipequaline, alone or in combination with diazepam. Psychopharmacology (Berl). 1988;95(3):386-9. PubMed PMID: 3137626.

2: Essassi D, Urien S, Zini R, Tillement JP. Pipequaline transport from blood to brain and liver: role of plasma protein-bound drug. J Pharm Pharmacol. 1989 Sep;41(9):595-600. PubMed PMID: 2573702.

3: 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. PubMed PMID: 2823163.

4: Eves FF, Lader MH. The effects of alcohol on psychological functions in normal volunteers after 8 days' treatment with pipequaline (PK 8165), diazepam or placebo. Eur J Clin Pharmacol. 1989;36(1):47-52. PubMed PMID: 2917587.

5: Essassi D, Zini R, Hamberger C, Urien S, Rougeot C, Uzan A, Tillement JP. Binding in vitro of pipequaline (45319 RP) onto plasma proteins and blood cells in man. Biochem Pharmacol. 1987 Oct 15;36(20):3501-7. PubMed PMID: 2890351.

6: von Frenckell R, Ansseau M, Bonnet D. Evaluation of the sedative properties of PK 8165 (pipequaline), a benzodiazepine partial agonist, in normal subjects. Int Clin Psychopharmacol. 1986 Jan;1(1):24-35. PubMed PMID: 3559150.

7: Essassi D, Zini R, Tillement JP. Use of 1-anilino-8-naphthalene sulfonate as a fluorescent probe in the investigation of drug interactions with human alpha-1-acid glycoprotein and serum albumin. J Pharm Sci. 1990 Jan;79(1):9-13. PubMed PMID: 2313585.

8: Lan NC, Chen JS, Johnson D, Gee KW. Differential effects of 4'-chlorodiazepam on expressed human GABAA receptors. J Neurochem. 1995 Feb;64(2):684-8. PubMed PMID: 7830061.

9: Essassi D, Zini R, Tillement JP. ANS-drug interactions to AAG and HSA fluorescence and equilibrium dialysis studies. Prog Clin Biol Res. 1989;300:423-6. PubMed PMID: 2780639.

10: Gee KW. 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. J Pharmacol Exp Ther. 1987 Mar;240(3):747-53. PubMed PMID: 3031273.

11: Simmonds MA. Antagonism of flurazepam and other effects of Ro15-1788, PK8165 and Ro5-4864 on the GABA-A receptor complex in rat cuneate nucleus. Eur J Pharmacol. 1985 Oct 29;117(1):51-60. PubMed PMID: 3002803.

12: File SE, Pellow S. The effects of putative anxiolytic compounds (PK 8165, PK 9084 and tracazolate) on the rat corticosterone response. Physiol Behav. 1985 Oct;35(4):583-6. PubMed PMID: 2866553.

13: 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. PubMed PMID: 6097832.

14: Gee KW, Brinton RE, Yamamura HI. PK 8165 and PK 9084, two quinoline derivatives with anxiolytic properties, antagonize the anticonvulsant effects of diazepam. Brain Res. 1983 Mar 28;264(1):168-72. PubMed PMID: 6303496.

15: File SE, Lister RG. Quinolines and anxiety: anxiogenic effects of CGS 8216 and partial anxiolytic profile of PK 9084. Pharmacol Biochem Behav. 1983 Feb;18(2):185-8. PubMed PMID: 6132404.

16: Gee KW, Yamamura HI. Selective anxiolytics: are the actions related to partial "agonist" activity or a preferential affinity for benzodiazepine receptor subtypes? Adv Biochem Psychopharmacol. 1983;38:1-9. PubMed PMID: 6142598.

17: Najim RA, al-Essa LY, al-Jawad FH. Effect of some drugs acting at the central-type benzodiazepine receptors on blood glucose in mice. Clin Exp Pharmacol Physiol. 1989 Jan;16(1):7-12. PubMed PMID: 2539928.

18: 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. PubMed PMID: 3703176.

19: Pellow S, File SE. Anxiolytic and anxiogenic drug effects on exploratory activity in an elevated plus-maze: a novel test of anxiety in the rat. Pharmacol Biochem Behav. 1986 Mar;24(3):525-9. PubMed PMID: 2871560.

20: Pellow S, File SE. Pro- and anti-convulsant drug effects in combination with the convulsant benzodiazepine Ro 5-4864. J Pharm Pharmacol. 1985 Aug;37(8):560-3. PubMed PMID: 2864417.