Nitrogen-based toxins

It remained to establish the manner of linkage of the two portions of the molecule represented by the known cleavage products, von Miller and Rohde had rediscovered a reaction first observed by Pasteur (70), namely, that the bitertiary bases cinchonine and quinine were converted under acidic conditions into ketones, designated as toxines, which contained a secondary amine function, and in order to explain these observations, made the fruitful suggestion that the non-aromatic moiety of the alkaloid molecules contained a bicyclic system with nitrogen at the... 

This view of the nature of the process is confirmed by the behavior of the quaternary salts (XXXII) derived from the alkaloids (81-87). These substances very readily undergo transformation to AT-alkyl toxines (XXXIII) in the presence of bases alone. In these cases, a full positive charge is fixed on the nitrogen atom, and the base-catalyzed removal of H-C.9 alone initiates reaction. It is of interest that base-... 

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