There is much research now on cannabinoids, but I have not seen any of these yet. I would like some company to give me a lab for this, otherwise someone else(s) gonna do it in their garage ……

Starting with THC, [I], hydroboration-oxidation produces the alcohol , [II], in anti-Markovnikov orientation:

Oxidation by any number of methods easily yields the ketone, [III]. Use of the mild hypervalent iodine reagent may be best to avoid opening the center ring to form the CBD analog:

Then standard reductive animation yields the amine; any other amine as well as the unsubstituted can also form by this method:

Note that [IV] has the core structure of many stimulants, psychedelics as well as legitimate antidepressants. You see phenyl-isopropyl(methyl)amine accented in bold, and the usual type substituent’s on the ring in blue.

I expect compounds [II] and [III] to be active, probably as mild neuroleptics, maybe psycho-stimulant or antidepressant. Compound [IV] should be very interesting ……


However, if it is found to have no legitimate medical use, it might move into the "ecstacy" market share ...... and since it is made from (legal and getting legaler) THC, legality may not be an issue. Also, if it displaces ecstacy, all the sassafras trees in SE Asia can be spared, along with the associated environmental destruction!

And of course with all of these, the center ring can be opened with acid under the right conditions to form the corresponding CBD analogs. The THC <-> CBD transformation is reversible, equilibrium, it can go either way depending on tweaking the reaction conditions. Thus with all of these derivatives, both analogs can be made.

For the corresponding isomers, simple hydrolysis or mild acid addition can functionalize the tertiary position:

Compound [V] should be active as well; compound [VI] would be chemically reactive and unstable, not pharmacologically useful itself, but as an intermediate to the amine; there are many ways to do this, here are two:

And these amines can reasonably be expected to have strong pharmacologic activity as well.

 

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