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.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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2-Naphthylamine / analogs & derivatives
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2-Naphthylamine / chemical synthesis*
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2-Naphthylamine / pharmacology
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Animals
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Cats
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Dogs
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Dopamine / physiology*
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Emetics / chemical synthesis
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Heart / innervation
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Heart Rate / drug effects
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Humans
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Male
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Naphthalenes / chemical synthesis*
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Rats
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Stereotyped Behavior / drug effects
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Structure-Activity Relationship
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Synaptic Transmission / drug effects
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Tetrahydronaphthalenes / chemical synthesis*
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Tetrahydronaphthalenes / pharmacology
Substances
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5-hydroxy-6-methyl-2-aminotetralin
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Emetics
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Naphthalenes
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Tetrahydronaphthalenes
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2-Naphthylamine
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Dopamine