Synthesis and pharmacology of new psychoactive substance 5F-CUMYL-P7AICA, a scaffold- hopping analog of synthetic cannabinoid receptor agonists 5F-CUMYL-PICA and 5F-CUMYL-PINACA

Drug Testing and Analysis
Samuel D BanisterRoy R Gerona

Abstract

Synthetic cannabinoid receptor agonists (SCRAs) are a dynamic class of new psychoactive substances (NPS), with novel chemotypes emerging each year. Following the putative detection of 5F-CUMYL-P7AICA in Australia in 2016, the scaffold-hopping SCRAs 5F-CUMYL-PICA, 5F-CUMYL-PINACA, and 5F-CUMYL-P7AICA were synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). Since little is known of the pharmacology of 7-azaindole SCRAs like 5F-CUMYL-P7AICA, the binding affinities and functional activities of all compounds at cannabinoid type 1 and type 2 receptors (CB1 and CB2 , respectively) were assessed using tritiated radioligand competition experiments and fluorescence-based plate reader membrane potential assays. Despite CB1 binding affinities differing by over two orders of magnitude (Ki  = 2.95-174 nM), all compounds were potent and efficacious CB1 agonists (EC50  = 0.43-4.7 nM), with consistent rank order for binding and functional activity (5F-CUMYL-PINACA >5F-CUMYL-PICA >5F-CUMYL-P7AICA). Additionally, 5F-CUMYL-P7AICA was found to exert potent cannabimimetic effects in mice, inducing hypothermia...Continue Reading

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Citations

Feb 12, 2020·British Journal of Clinical Pharmacology·Raquel Santos-ToscanoColin Davidson
Apr 7, 2020·Archives of Toxicology·Dino Luethi, Matthias E Liechti
Jun 14, 2019·Frontiers in Pharmacology·Richard C KevinSamuel D Banister
Oct 11, 2020·Drug Testing and Analysis·Sebastian HalterVolker Auwärter
Sep 1, 2019·Biochemical Pharmacology·Elise WoutersChristophe P Stove
Jan 2, 2021·Forensic Science International : Synergy·Nicole S Jones, Jeffrey H Comparin
Jan 29, 2021·Pharmacology, Biochemistry, and Behavior·Savanah L Saldaña-ShumakerChristopher W Cunningham
Jan 9, 2021·Therapeutic Advances in Psychopharmacology·Abu ShafiDerek K Tracy

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