Quipazine

Today, Quipazine is a topic of great interest and relevance in our society. For years now, Quipazine has captured the attention of experts and professionals in different fields, as well as the general public. The importance of Quipazine has been increasing as we enter an era of change and advancement in various areas. Whether in the technological, scientific, social, or cultural field, Quipazine has proven to be a topic of constant discussion and debate. In this article, we will explore different aspects related to Quipazine, from its impact on daily life to its influence on the future of society.

Quipazine
Clinical data
ATC code
  • none
Identifiers
  • 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)
  • 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.[citation needed]

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

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. ^ a b c 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).


Wikious
Boobota
Sagapedia