Optically pure (-)-4-[(N-allyl-3-methyl-4-piperidinyl)phenyl-amino]-N,N-diethylbenzami de displays selective binding and full agonist activity for the delta opioid receptor

Bioorg Med Chem Lett. 1999 Dec 6;9(23):3347-50. doi: 10.1016/s0960-894x(99)00613-7.

Abstract

The optical isomers of 4-[(N-allyl-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzamide+ ++ (3) have been prepared and tested in both binding and functional assays. The data show that (-)-3 is responsible for the delta opioid activity demonstrated by the racemic material. This compound displays a binding affinity of 5.5 nM for the delta opioid receptor as well as a 470-fold delta versus mu selectivity. Importantly, (-)-3 is a full agonist at the delta receptor in comparison with SNC-80 (2). Taken together, the data suggest that (-)-3 behaves more like the prototypical delta agonists, BW373U86 or SNC-80, and less like the peptidomimetic compound SL-3111 (5).

Publication types

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

MeSH terms

  • Benzamides / chemistry
  • Benzamides / metabolism*
  • Benzamides / pharmacology
  • Brain / metabolism
  • Piperidines / chemistry
  • Piperidines / metabolism*
  • Piperidines / pharmacology
  • Radioligand Assay
  • Receptors, Opioid, delta / drug effects
  • Receptors, Opioid, delta / metabolism*

Substances

  • 4-((N-allyl-3-methyl-4-piperidinyl)phenylamino)-N,N-diethylbenzamide
  • Benzamides
  • Piperidines
  • Receptors, Opioid, delta