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(+/-)-4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylben zamide displays selective binding for the delta opiod receptor

Racemic 4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzamide (3a) was synthesized and found to have good affinity and selectivity for the 6 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 6 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 [S-35]GTP gamma S functional assay suggests that 3a may be more like the peptide DPDPE. (C) 1999 Elsevier Science Ltd. All rights reserved


Thomas, J., Herault, X., Rothman, RB., Burgess, J., Mascarella, S., Xu, H., ... Carroll, F. (1999). (+/-)-4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylben zamide displays selective binding for the delta opiod receptor. Bioorganic and Medicinal Chemistry Letters, 9(20), 3053-3056.