Microsomal N-oxidation of long chain N,N-dimethylalkylamines: quantitative structure-activity relationships

N,N-Dimethylalkylamines CmH2m+1N(CH3)2 (m = 4 to 18) undergo in vitro N-oxidation to the corresponding amine oxides by mouse liver microsomes. The relative oxidisability of these compounds is parabolically dependent on structural and physico-chemical characteristics (with a maximum at m 12) and is controlled by at least three factors: lipophilicity, stereochemistry and the nucleophilicity of the compounds under evaluation. The results from the QSAR study support this multifactorial view.