title: Conformation of 2,9-dimethyl-3'-hydroxy-5-phenyl-6,7-genzomorphan and its relation to other analgetics and enkephalin.
abstract: X-ray crystallographic data for 2,9-dimethyl-3'-hydroxy-5-phenyl-6,7-benzomorphan (I) as its p-bromobenzoyl ester are presented. The structure of I is compared with that of morphine, meperidine, alpha-allylprodine, methadone, and moramide as well as with a proposed structure of the enkephalins. A quantitative relationship is found between in vitro opiate receptor binding potency and in vivo analgesia for analgesics of diverse structure, including I. A new view of the analgetic pharmacophore is presented. Programs for the TI Programmable 59 calculator are described for conversion of X-ray crystallographic data to rectangular coordinates with reorientation of the molecule and for the calculation of torsion angles.
mesh_terms: D000698:Analgesia; D000700:Analgesics / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D001921:Brain / Q000378:metabolism / Q000648:ultrastructure; D003201:Computers; D003461:Crystallography; D004723:Endorphins / Q000378:metabolism / Q000494:pharmacology; D004745:Enkephalins / Q000378:metabolism / Q000494:pharmacology; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D008954:Models, Biological; D008958:Models, Molecular; D008968:Molecular Conformation; D009019:Morphinans / Q000378:metabolism / Q000494:pharmacology*; D011809:Quinones / Q000037:antagonists & inhibitors; D051381:Rats; D011957:Receptors, Opioid / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000700:Analgesics; D004723:Endorphins; D004745:Enkephalins; D009019:Morphinans; D011809:Quinones; D011957:Receptors, Opioid