Abstract
The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.
Publication types
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Comparative Study
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Apomorphine / pharmacology
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Aporphines / chemical synthesis*
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Aporphines / metabolism
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Aporphines / pharmacology
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Arousal / drug effects
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Binding, Competitive
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Chemical Phenomena
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Chemistry
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Corpus Striatum / metabolism
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Dopamine Antagonists*
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Male
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Rats
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Rats, Inbred Strains
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Receptors, Dopamine / drug effects
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Receptors, Dopamine / metabolism*
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Stereoisomerism
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Stereotyped Behavior / drug effects
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Structure-Activity Relationship
Substances
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Aporphines
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Dopamine Antagonists
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Receptors, Dopamine
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11-hydroxy-N-(n-propyl)noraporphine
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Apomorphine