Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids

Shane M. Wilkinson A , Samuel D. Banister A B C and Michael Kassiou A B D E
+ Author Affliations
- Author Affliations

A School of Chemistry, Sydney University, Sydney, NSW 2006, Australia.

B Brain and Mind Research Institute, 100 Mallett St, Camperdown, NSW 2050, Australia.

C Department of Radiology, Stanford University School of Medicine, Stanford, CA 94305, USA.

D Faculty of Health Science, Sydney University, Sydney, NSW 2006, Australia.

E Corresponding author. Email: michael.kassiou@sydney.edu.au

Australian Journal of Chemistry 68(1) 4-8 https://doi.org/10.1071/CH14198
Submitted: 1 April 2014  Accepted: 15 April 2014   Published: 22 May 2014

Abstract

Over the past decade, a plethora of indole-based synthetic cannabinoids (SCs) have emerged with their structures clearly inspired by scientific literature. Their structures continually evolve to elude detection by law enforcement and circumvent finite scheduling laws. The latest generation of SCs follow patent literature that encompasses a bioisosteric fluorine-for-hydrogen replacement commonly applied in medicinal chemistry. Unlike traditional pharmaceutical development, where rigorous preclinical evaluation is completed before human administration, these SCs are distributed for intended recreational consumption with little-to-no pharmacological data known. This highlight explores the evolution of SCs to this latest generation of fluorinated SCs where accumulating evidence indicates increased health concerns.


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