3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties

Bioorg Med Chem Lett. 2001 Jul 9;11(13):1717-21. doi: 10.1016/s0960-894x(01)00278-5.


In response to the unexpectedly high affinity for opioid receptors observed in a novel series of cyclazocine analogues where the prototypic 8-OH was replaced by a carboxamido group, we have prepared the corresponding 3-CONH(2) analogues of morphine and naltrexone. High affinity (K(i)=34 and 1.7nM) for mu opioid receptors was seen, however, the new targets were 39- and 11-fold less potent than morphine and naltrexone, respectively.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amides / chemistry*
  • Morphine Derivatives / chemical synthesis
  • Morphine Derivatives / chemistry*
  • Morphine Derivatives / metabolism
  • Naltrexone / analogs & derivatives*
  • Naltrexone / chemical synthesis
  • Naltrexone / metabolism
  • Protein Binding
  • Receptors, Opioid / metabolism*


  • Amides
  • Morphine Derivatives
  • Receptors, Opioid
  • Naltrexone