meperidine and cocaine

[hussness]

I was just glancing through a few journal articles and noticed that some research has been done recently on meperidine analogs as far as binding to DAT, NET, and SERT. A couple of references are below:

J. Med. Chem. 2005, 48, 1336-1343.
J. Org. Chem. 1998, 63, 418-419.

Anyway, I've posted the structures of nocaine, meperidine, and a compound that I don't think has been studied that I was playing around with in chemdraw. I was wondering if it would be theoretically possible to get a compound that was an H-bond donor in the all of the right places such that it would bind with high affinity to DAT, and also to NET, SERT, and have affinity for the mu opioid receptor -- I guess sort of a theoretical speedball all wrapped up into one compound?

 

[hussness]

Sorry, I didn't mean to attach three duplicate gifs.

 

[BilZ0r]

Whats meperidine's DAT-SERT-NET binding like?

 

[Smyth]

^shit, its an active sert inhibitor with poorish DAT activity and negligible NET activity.

Given the compound u posted is a peroxide it is gonna be potential of causing cellular damage. I saw such a functional group a while back for use in tumor therapy.

I dont see why u would want to retain mu agonism in the resultant compound since current theory dictates that this has a suppressant effect on its ability to function as a psycho-/loco-motor stimulant in behavioral modalities.

 

[BilZ0r]

^ I was just wondering about meperidines serotonin symdrome effects... thinking of a possible explanation.