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Forensic Toxicology
Published in: Forensic Toxicology 2/2019

Open Access 01-07-2019 | Cannabinoid | Original Article

New-generation azaindole-adamantyl-derived synthetic cannabinoids

Authors: Mitchell Longworth, Tristan A. Reekie, Karen Blakey, Rochelle Boyd, Mark Connor, Michael Kassiou

Published in: Forensic Toxicology | Issue 2/2019

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Abstract

Purpose

This work reports the synthesis and pharmacological and analytical data for a new series of recently identified azaindole-adamantyl-derived synthetic cannabinoids (SCs).

Methods

Each SC was synthesised using an efficient and divergent synthesis, and assessed by electron ionisation mass spectrometry (EIMS). The cannabimimetic activity of each compound was conducted using a fluorometric imaging plate reader (FLIPR) assay.

Results

The described EIMS method and retention time by gas chromatography were able to effectively differentiate each of the analogues regardless of the bicyclic core. For the first time in these SC structures, the bicyclic ring system was shown to have an impact on the cannabimimetic activities in the fluorometric assay of membrane potential. Analogues ranged from moderately potent at both CB1 and CB2 (e.g., AP4AIC EC50 = 160 nM and EC50 = 64 nM, respectively) to not active at either cannabinoid receptor (AP4AICA, AP5AICA, and APIC).

Conclusions

Further investigation into receptor selectivity surrounding these bicyclic cores could prove useful for future therapeutic applications.
Appendix
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Metadata
Title
New-generation azaindole-adamantyl-derived synthetic cannabinoids
Authors
Mitchell Longworth
Tristan A. Reekie
Karen Blakey
Rochelle Boyd
Mark Connor
Michael Kassiou
Publication date
01-07-2019
Publisher
Springer Singapore
Keyword
Cannabinoid
Published in
Forensic Toxicology / Issue 2/2019
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-019-00466-1

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