The interaction between 2'-deoxyadenosine and the model antitumor drug menadione has been studied in organic solvent and in micellar medium. The aim of the work is to elucidate the mechanism of this drug-nucleoside interaction and to determine the environmental effects. Laser flash photolysis and magnetic field effect are used to detect the transients and their spin states. The results indicate that H atom transfer and electron transfer are the operative mechanisms depending upon the medium.