Comparison of (-)-Eseroline with (+)-Eseroline and Dihydroseco Analogues in Antinociceptive Assays: Confirmation of Rubreserine Structure by X-ray Analysis

Article abstract of DOI:10.1021/jm00161a023

The enantiomers of eseroline bind to opiate receptors of rat brain membranes with equal affinities and show opiate agonist properties as inhibitors of adenylate cyclase in vitro.However, only (-)-eseroline shows potent narcotic agonist activity in vivo, similar to that of morphine.Neither (-)-noreseroline, (+)-eseroline, nor the open dihydroseco analogue (-)-8 shows analgetic effects in vivo.The structure of rubreserine being a resonance hybrid of an o-quinone with its zwitterionic mesomer is confirmed by solid-state X-ray diffraction analysis.