• Journal Article

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

Citation

Thomas, J., Atkinson, R., Herault, X., Rothman, R. B., Mascarella, S., Dersch, C. M., ... Carroll, F. (1999). Optically pure (-)-4-[(N-allyl-3-methyl-4-piperidinyl)phenyl-amino]-N,N-diethylbenzamid e displays selective binding and full agonist activity for the delta opioid receptor. Bioorganic and Medicinal Chemistry Letters, 9(23), 3347-3350.

Abstract

The optical isomers of 4-[(N-allyl-3-methyl-4-piperidiny)phenylamino]-N,N-diethylbenzamine (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 of SNC-80, and less like the peptidomimetic compound SL-3111 (5). (C) 1999 Elsevier Science Ltd. All rights reserved