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    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

    Access Status
    Fulltext not available
    Authors
    Banister, S.
    Adams, A.
    Kevin, R.
    Macdonald, C.
    Glass, M.
    Boyd, R.
    Connor, M.
    McGregor, I.
    Havel, C.
    Bright, S.
    Vilamala, M.
    Lladanosa, C.
    Barratt, Monica
    Gerona, R.
    Date
    2018
    Type
    Journal Article
    
    Metadata
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    Citation
    Banister, S. and Adams, A. and Kevin, R. and Macdonald, C. and Glass, M. and Boyd, R. and Connor, M. et al. 2018. 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.
    Source Title
    Drug Testing and Analysis
    DOI
    10.1002/dta.2491
    ISSN
    1942-7603
    School
    National Drug Research Institute (NDRI)
    URI
    http://hdl.handle.net/20.500.11937/71444
    Collection
    • Curtin Research Publications
    Abstract

    © 2018 John Wiley & Sons, Ltd. 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 (6°C, 3 mg/kg) through a CB1-dependent mechanism.

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