title: Syntheses, analgetic activity, and physical dependence capacity of 5-phenyl-6,7-benzomorphan derivatives.
abstract: The synthesis, analgetic activity, and physical dependence 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-delta 3-piperidinium salt derivatives (V) under various conditions are discussed. The absolute configuration of the 9-demethyl series and the 2'-deoxy series is established by comparison of their ORD and CD spectra with those of 49, 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.
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D004347:Drug Interactions; D000882:Haplorhini; D006801:Humans; D008722:Methods; D051379:Mice; D009019:Morphinans / Q000138:chemical synthesis*; D009020:Morphine / Q000494:pharmacology; D009270:Naloxone / Q000494:pharmacology; D011809:Quinones / Q000037:antagonists & inhibitors; D011930:Reaction Time / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013375:Substance Withdrawal Syndrome / Q000139:chemically induced
chemical_list: D000701:Analgesics, Opioid; D001575:Benzomorphans; D009019:Morphinans; D011809:Quinones; D009270:Naloxone; D009020:Morphine