Rigid congeners of dopamine based on octahydrobenzo[f]quinoline: peripheral and central effects

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Abstract
A series of cis- and trans-dihydroxyoctahydrobenzo[f]quinoline congeners of dopamine was prepared, in which the N substituent was H, ethyl or n-propyl. The trans isomers include the dopamine moiety held rigidly in an antiperiplanar disposition which was believed to be necessary for certain central and peripheral dopaminergic effects. The cis isomers were flexible molecules; the dopamine moiety lacks conformational integrity and it could exist in a conformation which was believed not to favor dopaminergic activity. The trans series of compounds possessed a high level of central and peripheral dopaminergic effects on dog, pigeon, cat, rat and mouse, whereas the cis series was of low activity or was inert.