Opiate receptor interaction of compounds derived from or structurally related to fentanyl

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Abstract
The opiate receptor affinity of compounds derived from or structurally related to fentanyl was determined by in vitro [rat brain] receptor binding assays. The relatively high affinity of fentanyl (3 times morphine) was hardly influenced by the introduction of a 2-CH3, 2-OCH3 or a 2-Cl substituent into the anilino phenyl and was moderately reduced by 2-C2H5, 2-OC2H5 and 2,6-C(CH3)2 substitution in this ring. Removal of the N-propionyl group of the 2-OCH3 derivative fixation of the anilino phenyl in fentanyl to the propionyl group or the piperidine ring and replacement of the amide N by C all caused a sharp decline of receptor affinity. Examination of molecular models seemed to indicate that optimal opiate receptor interaction of fentanyl and its derivatives requires a virtually perpendicular position of the anilino phenyl with respect to the amide function.

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