(+/-)-4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzamide displays selective binding for the delta opioid receptor.
Racemic 4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzam ide (3a) was synthesized and found to have good affinity and selectivity for the delta receptor. These compounds can be viewed as an analog of BW373U86 and SNC-80 where an internal piperazine nitrogen has been transposed with a benzylic carbon. Functionally, 3a behaves as an agonist at the delta receptor with no measurable stimulation of either the mu or kappa receptor subtypes and was found to be devoid of any measurable amount of antagonist activity for any opioid receptor. A comparison of 3a to SNC-80 and DPDPE in the [35S]GTPgammaS functional assay suggests that 3a may be more like the peptide DPDPE.
Thomas
J B
JB
Chemistry and Life Sciences, Research Triangle Institute, Research Triangle Park, NC 27709, USA.
Herault
X M
XM
Rothman
R B
RB
Burgess
J P
JP
Mascarella
S W
SW
Xu
H
H
Horel
R B
RB
Dersch
C M
CM
Carroll
F I
FI
D001549:Benzamides / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D010879:Piperazines / Q000378:metabolism; D010880:Piperidines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000819:agonists / Q000378:metabolism*
C401942:4-((N-allyl-3-methyl-4-piperidinyl)phenylamino)-N,N-diethylbenzamide; D001549:Benzamides; D010879:Piperazines; D010880:Piperidines; D017465:Receptors, Opioid, delta; C083877:BW 373U86; C088464:4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide