Catechol derivatives of 6-aminobenzocycloheptene: assessment of dopaminergic effects

The title compounds were prepared as congeners of the dopaminergically potent 2-amino-5,6-dihydroxytetralin series ("A-5,6-DTN"). None of the variously nitrogen-substituted benzocycloheptenes demonstrated any dopamine-like effects in a variety of assays. The primary amine had alpha 1-adrenoceptor stimulant effects. This lack of dopaminergic effect parallels the inactivity found in 6-aminobenzocycloheptenes bearing no oxygen substitutents, those bearing a single phenolic group, and those bearing a resorcinol 1,3-diphenolic substitution pattern.