Hi.
Look at these for a second:
They are both cocaine homologs, the one on the right is really cocaine, the one on the left is a proposed structure that has a few slight variations.
They are:
1.The six-membered piperidine portion of the bicyclic ring has been shortened to 5 members, making it a pyrrolidine ring. This changes the relative positioning of the two ring substituents, the methyl carboxylate, and the benzoate relative to the nitrogen. Before, the benzoate was para, and the methyl carboxylate was meta. Now, they can both be said to be "metapara" as the nitrogen is between both of them, visually, when depicted as a 5 membered ring.
2.In the tropine portion of the ring, the ethyl bridge now has a double bond, making it an ethylene bridge.
What I would like to know/have opinions on, is: would the activity of this homolog be very different than cocaine itself? Do you think potency would decrease with these two changes? If the double bond is a problem, what about the same questions for the saturated version of this five-membered homolog? Is the six-carbon ring skeleton vital to cocaine's action and potency?
I know there are a number of cocaine analogs that have been synthesized, some stronger, some weaker, but I have never seen either of these. I am interested in these, most especially the unsaturated compund, because I can think of a novel method for its preparation that I have never seen before.
Also, is the N-methyl in these cocaine analogs vital to its function and potency? The unmethylated analog would be tens of times easier to produce than the N-methylated version.
Thanks for your answers/opinions.
PrimoPyro