Synthesis and in Vitro and in Vivo Activity of (−)-(1R,5R,9R)- and (+)-(1S,5S,9S)-N-Alkenyl-, -N-Alkynyl-, and -N-Cyanoalkyl-5,9-dimethyl-2‘-hydroxy-6,7-benzomorphan Homologues

Two of the synthesized (−)-(1R,5R,9R)-N-homologues (N-but-3-enyl- and N-but-3-ynyl-5,9-dimethyl-2‘-hydroxy-6,7-benzomorphan (9, 13)) were found to be about 20 times more potent than morphine in the mouse tail-flick assay (ED50 = 0.05 mg/kg), and (−)-(1R,5R,9R)-N-but-2-ynyl-5,9-dimethyl-2‘-hydroxy-6,...

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