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

J Med Chem. 1979 May;22(5):537-53. doi: 10.1021/jm00191a016.

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

  • Analgesics, Opioid / chemical synthesis*
  • Animals
  • Benzomorphans / analogs & derivatives
  • Benzomorphans / chemical synthesis*
  • Benzomorphans / pharmacology
  • Drug Interactions
  • Haplorhini
  • Humans
  • Methods
  • Mice
  • Morphinans / chemical synthesis*
  • Morphine / pharmacology
  • Naloxone / pharmacology
  • Quinones / antagonists & inhibitors
  • Reaction Time / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substance Withdrawal Syndrome / chemically induced

Substances

  • Analgesics, Opioid
  • Benzomorphans
  • Morphinans
  • Quinones
  • Naloxone
  • Morphine