Comparative QSAR and radical toxicology: the aromatic CH2OH moiety

Evidence is summarized to show via quantitative structure-activity relation ships (QSAR) that the aromatic CH2OH group when conjugated with electron-re leasing substituents displays toxic effects that suggest a radical reaction mechanism. The evidence can be used to explain the inhibitory action of lu canthone toward schistosomiasis. That is, lucanthone per se is not active, but its metabolite in which a methyl group has been converted to CH2OH is. This calls to mind the activity of chloramphenicol, which was a very effect ive anti-bacterial agent, but also caused serious blood dyscrasias in some patients. Presumably this could have been due to the toxic action of radica ls.