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MedKoo Cat#: 329522 | Name: Pipequaline HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Pipequaline HCl
Pipequaline HCl
CAS#80221-58-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 329522

Name: Pipequaline HCl

CAS#: 80221-58-5 (HCl)

Chemical Formula: C22H25ClN2

Exact Mass: 0.0000

Molecular Weight: 352.91

Elemental Analysis: C, 74.88; H, 7.14; Cl, 10.05; N, 7.94

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
200mg USD 650.00 2 Weeks
500mg USD 1,450.00 2 Weeks
1g USD 1,950.00 2 Weeks
2g USD 3,450.00 2 Weeks
5g USD 5,850.00 2 Weeks
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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.
1: 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. doi: 10.1046/j.1471-4159.1995.64020684.x. PMID: 7830061. 2: 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. doi: 10.1002/jps.2600790104. PMID: 2313585. 3: 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. doi: 10.1111/j.2042-7158.1989.tb06538.x. PMID: 2573702. 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. doi: 10.1007/BF00561022. PMID: 2917587. 5: 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. PMID: 2780639. 6: 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. doi: 10.1111/j.1440-1681.1989.tb01902.x. PMID: 2539928. 7: 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. doi: 10.1007/BF00181953. PMID: 3137626. 8: 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. doi: 10.1016/0006-2952(87)90332-7. PMID: 2890351. 9: 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. 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. PMID: 3031273. 11: 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. doi: 10.1016/0028-3908(86)90252-2. PMID: 3703176. 12: 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. doi: 10.1016/0091-3057(86)90552-6. PMID: 2871560. 13: 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. doi: 10.1097/00004850-198601000-00004. PMID: 3559150. 14: 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. doi: 10.1016/0014-2999(85)90471-6. PMID: 3002803. 15: 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. doi: 10.1016/0031-9384(85)90144-1. PMID: 2866553. 16: 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. doi: 10.1111/j.2042-7158.1985.tb03067.x. PMID: 2864417. 17: 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. 18: File SE, Wilks L. Effects of acute and chronic treatment on the pro- and anti-convulsant actions of CL 218, 872, PK 8165 and PK 9084, putative ligands for the benzodiazepine receptor. J Pharm Pharmacol. 1985 Apr;37(4):252-6. doi: 10.1111/j.2042-7158.1985.tb05054.x. PMID: 2860223. 19: File SE. Modification of seizures elicited by the benzodiazepine Ro 5-3663-- a comparison with picrotoxin. J Pharm Pharmacol. 1984 Dec;36(12):837-40. doi: 10.1111/j.2042-7158.1984.tb04888.x. PMID: 6151978. 20: 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. doi: 10.1016/0028-3908(84)90229-6. PMID: 6097832.