Quipazine is a serotonergic drug of the piperazine group which is used in scientific research.[1] It was originally intended as an antidepressant but never developed for medical use.[1][additional citation(s) needed]
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| ECHA InfoCard | 100.164.885 |
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| Formula | C13H15N3 |
| Molar mass | 213.284 g·mol−1 |
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Pharmacology
editPharmacodynamics
editQuipazine is a serotonin reuptake inhibitor,[2] and also a moderately selective serotonin receptor agonist, binding to a range of different serotonin receptors, but particularly to the 5-HT2A[3] and 5-HT3 subtypes.[1][4][5] Activation of the serotonin 5-HT3 is implicated in inducing nausea and vomiting.[1]
Quipazine produces a head-twitch response and other psychedelic-consistent effects in animal studies including in mice, rats, and monkeys.[1][6] 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.[7][6] However Alexander Shulgin claimed that a fully effective psychedelic dose could be reached by blocking 5-HT3 receptors using a 5-HT3 antagonist.[8][6]
Chemistry
editQuipazine is synthesized by reacting 2-chloroquinoline with piperazine.
See also
editReferences
edit- ^ a b c d e Glennon, Richard A.; Dukat, Maƚgorzata (2 May 2023). "Quipazine: Classical hallucinogen? Novel psychedelic?". Australian Journal of Chemistry. 76 (5): 288–298. doi:10.1071/CH22256. ISSN 0004-9425.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Winter JC (1994). "The stimulus effects of serotonergic hallucinogens in animals". NIDA Research Monograph. 146: 157–82. PMID 8742798.
- ^ 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.
- ^ DE 2006638, Rodriguez R, issued 1970 Chem. Abstr., 73: 98987g (1970).