Quipazine

Quipazine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 2-piperazin-1-ylquinoline
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.164.885 Edit this at Wikidata
Chemical and physical data
FormulaC13H15N3
Molar mass213.284 g·mol−1
3D model (JSmol)
SMILES
  • C1CN(CCN1)C2=NC3=CC=CC=C3C=C2
InChI
  • 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
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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,[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. ↑ Cappelli A, Giuliani G, Gallelli A, Valenti S, Anzini M, Mennuni L, et al. (May 2005). "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. doi:10.1016/j.bmc.2005.03.008. PMID 15848758.
  2. ↑ Smith RL, Barrett RJ, Sanders-Bush E (November 1995). "Neurochemical and behavioral evidence that quipazine-ketanserin discrimination is mediated by serotonin2A receptor". The Journal of Pharmacology and Experimental Therapeutics. 275 (2): 1050–7. PMID 7473132.
  3. ↑ Cappelli A, Anzini M, Vomero S, Mennuni L, Makovec F, Doucet E, et al. (February 1998). "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. doi:10.1021/jm970645i. PMID 9513601.
  4. ↑ Cappelli A, Butini S, Brizzi A, Gemma S, Valenti S, Giuliani G, et al. (2010). "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. doi:10.2174/156802610791111560. PMID 20166948.
  5. 1 2 3 de la Fuente Revenga M, Shah UH, Nassehi N, Jaster AM, Hemanth P, Sierra S, Dukat M, González-Maeso J (January 2021). "Psychedelic-like Properties of Quipazine and Its Structural Analogues in Mice". ACS Chemical Neuroscience. 12 (5): 831–844. doi:10.1021/acschemneuro.0c00291. PMC 7933111. PMID 33400504.
  6. ↑ Winter JC (1994). "The stimulus effects of serotonergic hallucinogens in animals". NIDA Research Monograph. 146: 157–82. PMID 8742798.
  7. ↑ Halberstadt AL, Geyer MA (2016). "Effect of Hallucinogens on Unconditioned Behavior". Current Topics in Behavioral Neurosciences. 36: 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459.
  8. ↑ DE 2006638, Rodriguez R, issued 1970 Chem. Abstr., 73: 98987g (1970).


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