Author  Topic:   Fentanyl analogue 
hypo
Member   posted 12-25-1999 10:53 AM          
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I stumbled on this article: Iwasawa Y. et al: J. Med. Chem. 42/25 (Dec. 16), 1, (1999).
It describes opioid antagonists of fentanyl class. But compound 13 seems to be pretty good, unselective agonist binder (low nanomolar binding constants). The compound has alpha(o-chlorophenethyl) on 1-N (instead of beta phenethyl) and 2-benzimidazolone-1-yl instead of N-phenylpropionamide. Does anyone have an idea how this substitution pattern can affect the bioactivity?
Did anyone try to put an OH group in meta or ortho-position of the aniline phenyl?
Appreciate your input.

This seems to be a very special opioid agonist, because it does not bind to any of the ordinary opioid receptors, but instead the ORL-1 receptor. Read the article at

https://www.thevespiary.org/rhodium/Rhodium/pdf/orl1.agonist.pdf

Compound 13 is the agonist, the others are antagonists.

This is a nice review of the different kind of opioid receptors:

http://www.tocris.com/opioidreview.htm

There are also links to cannabinoid, dopamine, GABA, ... receptors - with a lot of refs.