ELECTROCHEMICAL OXIDATION OF METHYLENEDIOXYAMPHETAMINES

Four amphetamine derivatives bearing a methylenedioxy group at positio ns 3 and 4 of the benzene ring and differing in their substitution at C(6) were studied by differential pulse voltammetry in aqueous media. These experiments showed a single oxidation peak for the C(6)-H, -Br a nd -Cl compounds, while the C(6)-NO2 analogue was not oxidized. The ox idation peak is interpreted as due to the removal of one electron from the aromatic electrophore with formation of a radical cation stabiliz ed by the dioxole ring. The linear relationship between the peak curre nt and the concentration of the derivatives is appropriate for develop ment of a quantitative method for their determination. pK' values were determined using both electrochemical and spectrophotometric methods.