3-Methyl-PCPy

3-Me-PCPy
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-[1-(3-methylphenyl)cyclohexyl]pyrrolidine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H25N
Molar mass243.394 g·mol−1
3D model (JSmol)
  • CC1=CC(=CC=C1)C2(CCCCC2)N3CCCC3
  • InChI=1S/C17H25N/c1-15-8-7-9-16(14-15)17(10-3-2-4-11-17)18-12-5-6-13-18/h7-9,14H,2-6,10-13H2,1H3
  • Key:JZVMREFYFTZXGN-UHFFFAOYSA-N

3-Methyl-PCPy (3-Me-PCPy) is an arylcyclohexylamine derivative with an unusual spectrum of pharmacological effects, acting as both a potent NMDA antagonist and also a triple reuptake inhibitor which inhibits reuptake of all three monoamine neurotransmitters serotonin, dopamine and noradrenaline. It also acts as a high affinity sigma receptor ligand, selective for the σ2 subtype. It produces both stimulant and dissociative effects in animal behavioural studies.

Pharmacology

In in vitro binding assays, 3-Me-PCPy displays high affinities across monoamine reuptake transporters alongside the NMDA receptor complex. Unusually for an arylcyclohexylamine dissociative, its affinity for the serotonin transporter (SERT) is approximately ten-fold higher than its affinity for the NMDA receptor pore.

Binding affinities of 3-Me-PCPy (Wallach & Brandt, 2018)
Target siteAssay / SiteKi (nM)
Serotonin transporter (SERT)Monoamine reuptake5.6
Dopamine transporter (DAT)Monoamine reuptake39.0
Norepinephrine transporter (NET)Monoamine reuptake45.0
NMDA receptorDizocilpine (MK-801) site52.3

3-Methyl-PCPy is covered by drug analogue laws in various jurisdictions (UK, Germany, Japan, Australia etc.) as a generic arylcyclohexylamine derivative, and a structural isomer of phencyclidine.

See also

References

  1. ↑ Wallach J, De Paoli G, Adejare A, Brandt SD (2014). "Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues". Drug Testing and Analysis. 6 (7–8): 633–50. doi:10.1002/dta.1468. PMID 23554350.
  2. ↑ Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID 24678061.
  3. 1 2 3 Wallach J, Brandt SD (2018). "Phencyclidine-Based New Psychoactive Substances". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 261–303. doi:10.1007/164_2018_124. ISBN 978-3-030-10560-0. PMID 30105474.