Synthesis of o-substituted derivatives of tetrahydrocannabinol with potential butyrylcholinesterase activity

Tetrahydrocannabinol is the major active constituent of cannabis sativa and has many medicinal properties. In present work, a pure compound, tetrahydrocannabinol (1) was isolated from the dark viscous oil of cannabis sativa by column chromatography using different solvent systems. The purified tetrahydrocannabinol compound (1) on further treatment with different electrophiles (2a-f) in the presence of sodium hydride and N,N-dimethyl formamide furnished O-substituted derivatives of tetrahydrocannabinol (3a-f). The structures of all the synthesized compounds have been deduced from their spectral (¹H NMR, IR and EI-MS) data. Further, all these compounds were screened against butyrylcholinesterase enzyme and found that these compounds displayed activity to varying degree.