Resolution and absolute configuration of the potent dopamine agonist N,N-diethyl-N'-[(3 alpha, 4a alpha, 10a beta)-1,2,3,4,4a,5,10,10a- -octahydro-6-hydroxy-1-propyl-3-benzo[g]quinolinyl]sulfamide.
The synthesis and preliminary pharmacological evaluation of the optical antipodes of the title compound (+/-)-1 (CV 205-502) is presented. The dopaminomimetic activity is shown to reside entirely in the (-) enantiomer. Crystallographic analysis has proven that the absolute configuration of the active (-) enantiomer corresponds to that of its ergoline analogue 3 (CQ 32-084) and of apomorphine (5).
D000634:Aminoquinolines / Q000494:pharmacology; D000818:Animals; D001058:Apomorphine / Q000494:pharmacology; D003461:Crystallography; D008297:Male; D008968:Molecular Conformation; D051381:Rats; D011954:Receptors, Dopamine / Q000187:drug effects*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000634:Aminoquinolines; D011954:Receptors, Dopamine; C046650:quinagolide; D001058:Apomorphine