posted on 2023-12-30, 04:29authored byEvangelos Dadiotis, Meng Cui, Maria Gerasi, Vangelis Mitsis, Eleni Melliou, Alexandros Makriyannis, Diomedes E. Logothetis, Prokopios Magiatis
In
recent years, the enantiomeric ratio of cannabichromene (CBC)
within the cannabis plant has attracted significant attention. Cannabichromene
is one of the well-known cannabinoids found in cannabis, along with
THC (tetrahydrocannabinol) and CBD (cannabidiol). Cannabichromene
exists as a scalemic mixture, meaning it has two enantiomers, (S)-cannabichromene and (R)-cannabichromene,
with the ratio between these enantiomers varying among different cannabis
strains and even within individual plants. This study presents an
accurate and robust chiral NMR method for analyzing cannabichromene’s
enantiomeric ratio, a well-investigated cannabinoid with numerous
pharmacological targets. The use of Pirkle’s alcohol as the
chiral solvating agent (CSA) or, alternatively, the use of (S)-ibuprofen as a chiral derivatizing agent (CDA) facilitated
this analysis. Moreover, the chiral NMR method proves to be a user-friendly
tool, easily applicable within any NMR facility, and an expanded investigation
of cannabichromene chirality may provide insights into the origin,
cultivation, treatment, and processing of Cannabis sativa plants. This study also undertakes a pharmacological examination
of the (R)- and (S)-cannabichromenes
concerning their most extensively studied pharmacological target,
the TRPA1 channels, with the two enantiomers showing the same strong
agonistic effect as the racemic mixture.