title: Derivatives of 5-hydroxy-6-methyl-2-aminotetralin.
abstract: The title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation. A sequence leading to a key synthetic intermediate, 5-methoxy-6-methyl-2-tetralone, has been developed. In animal test models for dopamine-like effects, the title compounds demonstrated qualitative and quantitative differences from the isomeric 5-methyl-6-hydroxy-2-aminotetralins and from 5,6-dihydroxy-2-aminotetralins. Two of the compounds were potent in a cat cardioaccelerator nerve assay, which involves dopamine receptors.
mesh_terms: D015081:2-Naphthylamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002415:Cats; D004285:Dogs; D004298:Dopamine / Q000502:physiology*; D004639:Emetics / Q000138:chemical synthesis; D006321:Heart / Q000294:innervation; D006339:Heart Rate / Q000187:drug effects; D006801:Humans; D008297:Male; D009281:Naphthalenes / Q000138:chemical synthesis*; D051381:Rats; D013239:Stereotyped Behavior / Q000187:drug effects; D013329:Structure-Activity Relationship; D009435:Synaptic Transmission / Q000187:drug effects; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: C026118:5-hydroxy-6-methyl-2-aminotetralin; D004639:Emetics; D009281:Naphthalenes; D013764:Tetrahydronaphthalenes; D015081:2-Naphthylamine; D004298:Dopamine