Synthesis and pharmacology of 8-amino-3-(cyclopropylmethyl)-1,2,3,4,5,6-hexahydro-cis-6,11-dimethyl-2,6-methano-3-benzazocine and related compounds.
The little compound 1a has been prepared and was found to be a strong, orally active agonist with narcotic--antagonist properties. 1a was prepared by two independent routes: (1) nitration of volazocine and subsequent reduction and (b) a sequence involving dissolving metal reduction of cyclazocine methyl ether, followed by oximination and Semmler--Wolff rearrangement. Several analogues were prepared and tested.
D000700:Analgesics / Q000138:chemical synthesis; D000818:Animals; D003496:Cyclazocine / Q000031:analogs & derivatives*; D004305:Dose-Response Relationship, Drug; D051379:Mice; D009292:Narcotic Antagonists / Q000138:chemical synthesis; D051381:Rats; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship; D013997:Time Factors
C023462:8-aminocyclazocine; D000700:Analgesics; D009292:Narcotic Antagonists; D003496:Cyclazocine