Conformationally restricted congeners of dopamine derived from 2-aminoindan.
Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) 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. In contrast, 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.
D000818:Animals; D001667:Binding, Competitive; D002415:Cats; D002417:Cattle; D004285:Dogs; D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D004558:Electric Stimulation; D004639:Emetics; D005260:Female; D006321:Heart / Q000187:drug effects; D066298:In Vitro Techniques; D007189:Indans / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D007192:Indenes / Q000138:chemical synthesis*; D008297:Male; D008968:Molecular Conformation; D011954:Receptors, Dopamine / Q000378:metabolism; D013134:Spiperone / Q000378:metabolism; D013764:Tetrahydronaphthalenes / Q000378:metabolism
D004639:Emetics; D007189:Indans; D007192:Indenes; D011954:Receptors, Dopamine; D013764:Tetrahydronaphthalenes; C006545:2-aminoindan; D013134:Spiperone; C011639:ADTN; D004298:Dopamine