9-Hydroxy-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine derivatives as analgesics

Abstract
Three 1,3-dimethyl-9-hydroxy-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine derivatives (7-9) were synthesized and tested as analgesics. The synthesis of these compounds involved conversion of 1-methyl-7-methoxy-.beta.-tetralone (1) by Mannich reaction with MeNH2 and HCHO to give the 11-ketone 2, from which 7, 8 and 9, respectively, were obtained. These compounds have analgesic activity, and 7 was comparable to codeine in mice.

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