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Abandoned drugs
Quipazine
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    Quipazine

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    Quipazine
    Quipazine.png
    Clinical data
    ATC code
    • none
    Identifiers
    • 2-piperazin-1-ylquinoline
    CAS Number
    PubChem CID
    IUPHAR/BPS
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.164.885
    Chemical and physical data
    Formula C13H15N3
    Molar mass 213.284 g·mol−1
    3D model (JSmol)
    • C1CN(CCN1)C2=NC3=CC=CC=C3C=C2
    • InChI=1S/C13H15N3/c1-2-4-12-11(3-1)5-6-13(15-12)16-9-7-14-8-10-16/h1-6,14H,7-10H2 ☒N
    • Key:XRXDAJYKGWNHTQ-UHFFFAOYSA-N ☒N
     ☒NcheckY (what is this?)  (verify)

    Quipazine is a serotonergic drug of the piperazine group which is used in scientific research. It was originally intended as an antidepressant but never developed for medical use.

    Pharmacology

    Pharmacodynamics

    Quipazine is a serotonin reuptake inhibitor, and also a moderately selective serotonin receptor agonist, binding to a range of different serotonin receptors, but particularly to the 5-HT2A and 5-HT3 subtypes.

    Quipazine produces a head-twitch response and other psychedelic-consistent effects in animal studies including in mice, rats, and monkeys. However, it failed to produce psychedelic effects in humans at a dose of 25 mg, which was the highest dose tested due to 5-HT3 mediated side effects of nausea and gastrointestinal discomfort. However Alexander Shulgin claimed that a fully effective psychedelic dose could be reached by blocking 5-HT3 receptors using a 5-HT3 antagonist.

    Chemistry

    Quipazine is synthesized by reacting 2-chloroquinoline with piperazine.

    Quipazine synthesis:

    See also



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