Conformationally restricted congeners of dopamine derived from 2-aminoindan

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Abstract
Two series of N-substituted 2-aminoindan systems were prepared: 4,5-dihydroxy-2-aminoindan has a hydroxylation pattern analogous to the .alpha. conformer of dopamine, and 5,6-dihydroxy-2-aminoindan has a hydroxylation pattern of the .beta. conformer of dopamine. All members of both series demonstrated only extremely weak binding to calf caudate homogenate. Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat. The 5,6-dihydroxy series displayed low or no activity/potency in these assays. Conformational analysis of the 2-aminoindan system is described and discussed.