Real public health problem, cancer is one of the pathologies that mobilize the entire scientific community. The conception of effective drugs against this pathology has become a challenge for all actors in research. Some molecules such as makaluvamines have shown important anticancer properties. These molecules belong to the family of alkaloids generally active in charged forms. The purpose of our work is to determine the protonation or methylation sites, relative stability and reactivity potential of some makaluvamines by a quantum chemistry method. B3LYP/6-311++G(d,p) theory level is used for all the calculations done. Firstly, we have estimated the gas phase basicity (GB) and proton affinity (PA) for the different heteroatoms of the molecules. Secondly, electronic energies, enthalpies of formation and free enthalpies of formation calculation permitted us to deduce the relative stability of the different forms of studied makaluvamines. Thirdly, Fukui functions, chemical softness and hardness, chemical potential and electrophilia index calculation lead us to the analysis of the reactivity. The results obtained permit us to identify the preferred site of protonation / methylation, to show that the charged forms are more stable and more reactive than the neutral forms.