Hans Bruderer

Two types of monoamine liberation by chlorinated aralkylamines

Abstract Two p-chlorinated aralkylamines (I and II) decrease the 5HT and NE in the brain of rats as well as the 5HT in platelets of rabbits and concomitantly increase 5-hydroxyindoleacetic acid and 5-hydroxytryptophol. The chemically related p-chloro-N, α-dimethylphenethylamine (III) causes, as previously described, a selective diminution of 5HT without increasing the 5HT metabolites. The two former drugs are about 10 times less potent than compound III in inhibiting the oxidative deamination of 5HT in vitro, but about 25 – 45 times more effective in liberating platelet 5HT. In the brain in vivo, III reaches higher levels than II. It is concluded that drug-induced differences in the rate of oxidative deamination of liberated 5HT might be responsible for the different metabolic pattern of the amine.

Synthesis in the emetine series—XIV : A new synthesis of 2,3,11-trisubstituted berbines

Abstract A new synthesis of 2,3,11-trisubstituted berbines is described. By this method the dimethoxysubstituted benzoquinolizidine keto ester I is annealted with a four carbon unit, cyclized and aromatized in the presence of an alcohol to give the 2,3-dimethoxy-11-alkoxy-substituted berbines VIII, IX and X. The stereochemistry of the intermediate compounds has been elucidated by physical-chemical methods.