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  • Title: Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis.
    Author: Schönenberger B, Jacobson AE, Brossi A, Streaty R, Klee WA, Flippen-Anderson JL, Gilardi R.
    Journal: J Med Chem; 1986 Nov; 29(11):2268-73. PubMed ID: 3023611.
    Abstract:
    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.
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