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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
Thomas, J., Atkinson, R., Herault, X., Rothman, RB., Mascarella, S., Dersch, CM., Xu, H., Horel, RB., & 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.
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
