Structure via PubChem · Public domain (PubChem)
quipazine
Sign in to saveAlso known as 2-(1-piperazinyl)quinoline, 2-QP, 1-(2-quinolinyl)piperazine, 2-piperazinoquinoline
Quipazine, also known as 1-(2-quinolinyl)piperazine (2-QP), is a serotonergic drug of the arylpiperazine family and an analogue of 1-(2-pyridinyl)piperazine which is used in scientific research. It was first described in the 1960s and was originally intended as an antidepressant but was never developed or marketed for medical use. The effects of quipazine in humans include nausea, vomiting, gastrointestinal disturbances, diarrhea, and, at higher doses, psychedelic effects. Quipazine may represent the prototype of a novel structural class of psychedelic drugs.
Chemical data
- Formula
- C13H15N3
- Molecular weight
- 213.28 g/mol
- IUPAC name
- 2-piperazin-1-ylquinoline
- SMILES
- C1CN(CCN1)C2=NC3=CC=CC=C3C=C2
- InChIKey
- XRXDAJYKGWNHTQ-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 28.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,009 papers- Quipazine Elicits Swallowing in the Arterially Perfused Rat Preparation: A Role for Medullary Raphe Nuclei?International journal of molecular sciences · 2020
- Psychedelic-like Properties of Quipazine and Its Structural Analogues in Mice.ACS chemical neuroscience · 2021
- Acute intrathecal administration of quipazine elicits air-stepping behavior.Behavioural pharmacology · 2021
- The interactions of the 5-HT3 receptor with quipazine-like arylpiperazine ligands: the journey track at the end of the first decade of the third millennium.Current topics in medicinal chemistry · 2010
- Quipazine increases renin release by a peripheral hemodynamic mechanism.Journal of cardiovascular pharmacology · 1990
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 213.126597
Show 3 more facts
- chemical formula
- C₁₃H₁₅N₃
- canonical SMILES
- C1CN(CCN1)C2=NC3=CC=CC=C3C=C2
- Commons category
- Quipazine
via Wikidata · CC0
~8 min read
Encyclopedic overview
14 sectionsContents
- Use and effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Chemistry
- Synthesis
- History
- Society and culture
- Legal status
- Canada
- United States
- See also
- References
- External links
Quipazine, also known as 1-(2-quinolinyl)piperazine (2-QP), is a serotonergic drug of the arylpiperazine family and an analogue of 1-(2-pyridinyl)piperazine which is used in scientific research. It was first described in the 1960s and was originally intended as an antidepressant but was never developed or marketed for medical use. The effects of quipazine in humans include nausea, vomiting, gastrointestinal disturbances, diarrhea, and, at higher doses, psychedelic effects. Quipazine may represent the prototype of a novel structural class of psychedelic drugs.
==Use and effects== The effects and side effects of quipazine in humans have been described. At a dose of 25mg orally, they included nausea, flatulence, gastrointestinal discomfort, and diarrhea, with no LSD-like subjective effects. Higher doses were not assessed due to serotonin 5-HT3 receptor-mediated side effects of nausea and gastrointestinal discomfort. An anecdotal report in one or more subjects, in which the dose of quipazine was said to be 0.5mg (sic), described quipazine as producing low-dose mescaline-like effects followed by onset of dysphoria and nausea.
Excerpted from Wikipedia’s “quipazine” article, available under the CC BY-SA 4.0 licence.