The Development of a Novel Synthesis and Structure of Trifluoro-THC

Case ID:

2021-001

BACKGROUND

The endocannabinoid system is part of both the central and peripheral nervous systems, playing roles in physiological, cognitive, and immune functions. Research over the past three decades has helped parse receptor pathways and shown that cannabinoid compounds like tetrahydrocannabinol (THC) have potential as pharmaceutical structures. However, THC’s status as a natural product does limit its commercial viability as it cannot be patented. This represents a roadblock to THC-based drug discovery and development, despite research suggesting its potential usage in pharmaceuticals. Another factor slowing THC-product drug discovery is the bioactivity itself; the compounds do have a limited bioactivity, which can be increased via fluorination. Fluorinated pharmaceuticals show markedly increased bioactivity, and many drugs (e.g., antivirals and chemotherapies) rely on their fluorinated nature to deliver desired performance. There is a clear need to develop novel synthesis methods and THC-based compounds to advance pharmaceutical discovery.

SUMMARY OF TECHNOLOGY

Researchers at OSU and University of Regensburg have developed a novel synthesis and structure of trifluoro-THC. The synthesis method allows a highly fluorinated arene to be coupled to C-H arenes with concaminant dearomatization, lending itself to the synthesis of cannabinoid-like structures. Fluorinating this motif has historically been challenging, and the trifluoro structure has never been made previously. These advancements usher in an entirely novel biochemical space to be explored for drug discovery and development, as well as neurological research tools.