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2,3,4,5-Tetrahydro-1,5-methano-1H-3benzazepine (4) has been synthesized from 2,3-dioxobenzonorbornene. Oxidative cleavage of the diketone to cis-1,3-indandicarboxylic acid, followed by closure to the corresponding amhydride, conversion to the imide, and lithium aluminum hydride reduction, gave 4. Compound 4 and its N-derivatives show no analgesic activity in the mouse hot-plate assay and little antagonist activity in a tail-flick assay.
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Mazzocchi et al. (1979) studied this question.
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