Chemistry:Quipazine

From HandWiki
Short description: Chemical compound
Quipazine
Quipazine.png
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC13H15N3
Molar mass213.284 g·mol−1
3D model (JSmol)
 ☒N☑Y (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.[citation needed]

Pharmacology

Pharmacodynamics

Quipazine is a serotonin reuptake inhibitor,[1] and also a moderately selective serotonin receptor agonist, binding to a range of different serotonin receptors, but particularly to the 5-HT2A[2] and 5-HT3 subtypes.[3][4]

Quipazine produces a head-twitch response and other psychedelic-consistent effects in animal studies including in mice, rats, and monkeys.[5] 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.[6][5] However Alexander Shulgin claimed that a fully effective psychedelic dose could be reached by blocking 5-HT3 receptors using a 5-HT3 antagonist.[7][5]

Chemistry

Quipazine is synthesized by reacting 2-chloroquinoline with piperazine.

Quipazine synthesis:[8]

See also

References

  1. ↑ "Structure-affinity relationship studies on arylpiperazine derivatives related to quipazine as serotonin transporter ligands. Molecular basis of the selectivity SERT/5HT3 receptor". Bioorganic & Medicinal Chemistry 13 (10): 3455–60. May 2005. doi:10.1016/j.bmc.2005.03.008. PMID 15848758. 
  2. ↑ "Neurochemical and behavioral evidence that quipazine-ketanserin discrimination is mediated by serotonin2A receptor". The Journal of Pharmacology and Experimental Therapeutics 275 (2): 1050–7. November 1995. PMID 7473132. 
  3. ↑ "Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 1. Mapping the central 5-HT3 receptor binding site by arylpiperazine derivatives". Journal of Medicinal Chemistry 41 (5): 728–41. February 1998. doi:10.1021/jm970645i. PMID 9513601. 
  4. ↑ "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.". Curr Top Med Chem 10 (5): 504–26. 2010. doi:10.2174/156802610791111560. PMID 20166948. 
  5. ↑ 5.0 5.1 5.2 "Psychedelic-like Properties of Quipazine and Its Structural Analogues in Mice". ACS Chemical Neuroscience 12 (5): 831–844. January 2021. doi:10.1021/acschemneuro.0c00291. PMID 33400504. 
  6. ↑ "The stimulus effects of serotonergic hallucinogens in animals". NIDA Research Monograph 146: 157–82. 1994. PMID 8742798. 
  7. ↑ "Effect of Hallucinogens on Unconditioned Behavior". Current Topics in Behavioral Neurosciences 36: 159–199. 2016. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMID 28224459. 
  8. ↑ Rodriguez R, DE patent 2006638, issued 1970 Chem. Abstr., 73: 98987g (1970).




Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Quipazine&oldid=3711919"