Pipequaline

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Chemical compound

title: "Pipequaline" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["anxiolytics", "gabaa-receptor-positive-allosteric-modulators", "4-piperidinyl-compounds", "quinolines", "sedatives"] description: "Chemical compound" topic_path: "general/anxiolytics" source: "https://en.wikipedia.org/wiki/Pipequaline" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | verifiedrevid = 464207358 | IUPAC_name = 2-phenyl-4-(2-piperidin-4-ylethyl)quinoline | image = Pipequaline.svg | image_class = skin-invert-image | width = 180

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 77472-98-1 | ATC_prefix = none | ATC_suffix = | PubChem = 71219 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 64354 | UNII_Ref = | UNII = J3S205V4I2

| C=22 | H=24 | N=2 | smiles = n1c4c(c(cc1c2ccccc2)CCC3CCNCC3)cccc4 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = AMEWZCMTSIONOX-UHFFFAOYSA-N

Pipequaline (INN; development code 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.

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (January 1986). "Evaluation of the sedative properties of PK 8165 (pipequaline), a benzodiazepine partial agonist, in normal subjects". International Clinical Psychopharmacology.
  3. (March 1986). "The ability of PK 8165, a quinoline derivative, to reduce responses to a stressful situation in a double-blind study in man". Neuropharmacology.
  4. (1988). "The effects on memory of pipequaline, alone or in combination with diazepam". Psychopharmacology.
  5. (October 1984). "Pharmacological evidence that PK 8165 behaves as a partial agonist of brain type benzodiazepine receptors". Archives Internationales de Pharmacodynamie et de Therapie.
  6. (October 1984). "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.
  7. (September 1987). "Pipequaline acts as a partial agonist of benzodiazepine receptors: an electrophysiological study in the hippocampus of the rat". Neuropharmacology.

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anxiolyticsgabaa-receptor-positive-allosteric-modulators4-piperidinyl-compoundsquinolinessedatives