title: 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.
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).
authors.affiliation: Chemistry and Life Sciences, Research Triangle Institute, Research Triangle Park, NC 27709, USA.
authors.forename: J B
authors.initials: JB
authors.lastname: Thomas
authors.forename: R N
authors.initials: RN
authors.lastname: Atkinson
authors.forename: X M
authors.initials: XM
authors.lastname: Herault
authors.forename: R B
authors.initials: RB
authors.lastname: Rothman
authors.forename: S W
authors.initials: SW
authors.lastname: Mascarella
authors.forename: C M
authors.initials: CM
authors.lastname: Dersch
authors.forename: H
authors.initials: H
authors.lastname: Xu
authors.forename: R B
authors.initials: RB
authors.lastname: Horel
authors.forename: F I
authors.initials: FI
authors.lastname: Carroll
mesh_terms: D001549:Benzamides / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D001921:Brain / Q000378:metabolism; D010880:Piperidines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000187:drug effects / Q000378:metabolism*
chemical_list: C401942:4-((N-allyl-3-methyl-4-piperidinyl)phenylamino)-N,N-diethylbenzamide; D001549:Benzamides; D010880:Piperidines; D017465:Receptors, Opioid, delta