2,3,4,5,6,7-hexahydro-1,6-methano-1H-3-benzazonine derivatives as analgesics.
10-Methoxy- (10) and 10-hydroxy-3-methyl-2,3,4,5,6,7-hexahydro-1H-3-benzazonine (11) have been synthesized from 7-methoxy-alpha-tetralone (1) via the 1-aminomethyl compound 4, which was converted to the amino acid derivative 7. Hydrogenation and cyclization of 7 afforded the lactam 9, which was reduced with LiAlH4, followed by N-methylation to give 10, from which 11 was obtained. Compounds 10 and 11 have analgetic activity, and the former was found to be comparable to codeine.
D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001381:Azepines / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D011312:Pressure; D011930:Reaction Time / Q000187:drug effects
D000700:Analgesics; D001381:Azepines; D009281:Naphthalenes