H-1 -H-15 HMBC spectra of norditerpenoid alkaloids and their synthetic azabicyclic analogues were obtained to investigate the impacts of the through-space effect of steric compression, protonation, and formation of intramolecular hydrogen bonding on the N-15 NMR spectroscopy of these natural products and their piperidine-containing analogues. A rare N-15 NMR effect of steric compression is demonstrated in half-cage A/E-rings of norditerpenoid alkaloid free bases and their synthetic azabicyclic analogues, in which the distribution of the lone pair of electrons of the tertiary amine N-atom is sterically restricted by bridged cycloalkanes, e.g., cyclopentane, cyclohexane, and cycloheptane rings. This results in significant changes in the N-15 chemical shift, typically by at least similar to 10 ppm. The lone pair of electrons of the N-atom in the piperidine ring are sterically compressed whether the bridged cyclohexane ring adopts a chair or boat conformation. The( 15)N chemical shifts of 1 alpha-OMe norditerpenoid alkaloid free bases significantly increase (Delta delta(N) >= 15.6 ppm) on alkaloid protonation and thence the formation of an intramolecular hydrogen bond between N+-H and 1 alpha-OMe. The intramolecular hydrogen bonds between the N-atom and 1 alpha-OH of 1 alpha-OH norditerpenoid alkaloid free bases, karacoline, condelphine, and neoline stabilize their A-rings, adopting an unusual twisted-boat conformation, and they also significantly increase delta(N) of the tertiary amine N-atom.