Syntheses, analgetic activity, and physical dependence capacity of 5-phenyl-6,7-benzomorphan derivatives

Article abstract of DOI:10.1021/jm00191a016

The synthesis, analgetic activity, and physical dependent capacity of a large number of 5-phenyl-6,7-benzomorphan derivatives are described. Observations made during the Stevens' rearrangement of 1-benzyl-1-methyl-Δ³-piperidinium salt derivatives (V) under various conditions are discussed. The absolute configuration of the 9-dimethyl series and the 2'-deoxy series is established by comparison of their ORD and CD spectra with those of ι-β-2'-hydroxy-2,9-dimethyl-5-phenyl-6,7-benzomorphan, whose absolute configuration was previously established by X-ray crystallography. A convenient synthesis of ³H-labeled phenols using ³H₃PO₄ is described, as well as the preparation of ¹⁴C-labeled compounds by conventional methods.