Following our recent study on the usefulness of borospiropentanes as new potential high-energy materials, we propose a new series of substituted spiropentane molecules, the azaspiropentanes. Presented here are the results of our ab initio calculations at the MP2 and B3LYP levels of theory using the 6-311++G(d,p) basis set. Results include optimized structural parameters, enthalpies of formation, specific enthalpies of combustion, and proton affinities. Our results indicate that azaspiropentane gives off the most energy of any of the nitrogen-containing spiropentanes, as indicated by its specific enthalpy of combustion of −41 kJ g-1; however, it does not give off as much energy as spiropentane itself, which gives off about 48 kJ g-1.