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

Authors
Thomas, JB Atkinson, RN Herault, XM Rothman, RB Mascarella, SW Dersch, CM Xu, H Horel, RB Carroll, FI
Citation
Jb. Thomas et al., Optically pure (-)-4-[(N-allyl-3-methyl-4-piperidinyl)phenyl-amino]-N,N-diethylbenzamide displays selective binding and full agonist activity for thedelta opioid receptor, BIOORG MED, 9(23), 1999, pp. 3347-3350
Citations number
9
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
23
Year of publication
1999
Pages
3347 - 3350
Database
ISI
SICI code
0960-894X(199912)9:23<3347:OP(>2.0.ZU;2-8
Abstract
The optical isomers of 4-[(N-allyl-3-methyl-4-piperidiny)phenylamino]-N,N-d iethylbenzamine (3) have been prepared and tested in both binding and funct ional assays. The data show that (-)-3 is responsible for the delta opioid activity demonstrated by the racemic material. This compound displays a bin ding 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 d elta receptor in comparison with SNC-80 (2). Taken together, the data sugge st that (-)-3 behaves more like the prototypical delta agonists, BW373U86 o f SNC-80, and less like the peptidomimetic compound SL-3111 (5). (C) 1999 E lsevier Science Ltd. All rights reserved.