(.alpha.S)-erythro-.alpha.-Methylepinephrine: preparation and stereoselective binding to adrenergic receptors in rat forebrain

The enantiomers of a number of catecholamines, including (alpha S)- and (alpha R)-erythro-alpha-methylepinephrine, were evaluated for their capacity to compete for binding sites in rat forebrain homogenates with [3H]prazosin, a ligand which selectively binds to adrenergic receptors of the alpha 1 su...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1981-10, Vol.24 (10), p.1261-1263
Main Authors: Taylor, Clinton A, Smith, Howard E, Goldberg, Michael R, Robertson, David
Format: Article
Language:English
Subjects:
Animals
Brain - metabolism
Catecholamines - chemical synthesis
Catecholamines - metabolism
Circular Dichroism
Epinephrine - analogs & derivatives
Epinephrine - chemical synthesis
Epinephrine - metabolism
Prazosin - metabolism
Rats
Receptors, Adrenergic - metabolism
Stereoisomerism
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Summary:The enantiomers of a number of catecholamines, including (alpha S)- and (alpha R)-erythro-alpha-methylepinephrine, were evaluated for their capacity to compete for binding sites in rat forebrain homogenates with [3H]prazosin, a ligand which selectively binds to adrenergic receptors of the alpha 1 subtype. (alpha R)-erythro-alpha-Methylepinephrine is devoid of apparent biological activity, but the activity of the alpha S isomer is substantial. The latter is less active than the endogeneous catecholamines, (R)-norepinephrine and (R)-epinephrine, but the stereospecific competition for [3H]prazosin binding sites by the catecholamine isomers with the beta R configuration is additional evidence that (alpha S)-erythro-alpha-methylepinephrine may be a biologically active metabolite of L-alpha-methyl-3,4-dihydroxyphenylalanine.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00142a027