Quipazine

Chemical compound
  • none
Identifiers
  • 2-piperazin-1-ylquinoline
CAS Number
  • 4774-24-7 checkY
PubChem CID
  • 5011
IUPHAR/BPS
  • 173
ChemSpider
  • 4836 ☒N
UNII
  • 4WCY05C0SJ
ChEMBL
  • ChEMBL18772 ☒N
CompTox Dashboard (EPA)
  • DTXSID3046952 Edit this at Wikidata
ECHA InfoCard100.164.885 Edit this at WikidataChemical and physical dataFormulaC13H15N3Molar mass213.284 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒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,[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. ^ 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).


  • v
  • t
  • e
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transportersOthers
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
  • v
  • t
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5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • See also: Receptor/signaling modulators
  • Adrenergics
  • Dopaminergics
  • Melatonergics
  • Monoamine reuptake inhibitors and releasing agents
  • Monoamine metabolism modulators
  • Monoamine neurotoxins
  • v
  • t
  • e
Simple piperazines
(no additional rings)
Phenylpiperazines
Benzylpiperazines
Diphenylalkylpiperazines
(benzhydrylalkylpiperazines)
Pyrimidinylpiperazines
Pyridinylpiperazines
Benzo(iso)thiazolylpiperazines
Tricyclics
(piperazine attached via side chain)
Others/Uncategorized