title: Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis.
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.
mesh_terms: D000067956:Adenylyl Cyclase Inhibitors; D000700:Analgesics / Q000494:pharmacology*; D000818:Animals; D066298:In Vitro Techniques; D007211:Indoles / Q000494:pharmacology*; D010830:Physostigmine / Q000031:analogs & derivatives* / Q000494:pharmacology; D051381:Rats; D011957:Receptors, Opioid / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D000067956:Adenylyl Cyclase Inhibitors; D000700:Analgesics; D007211:Indoles; D011957:Receptors, Opioid; C027950:rubreserine; D010830:Physostigmine; C022594:eseroline