Conformational Analysis of the Anti-obesity Drug Lorcaserin in Water: How To Take Advantage of Long-Range Residual Dipolar Couplings

The conformational state of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (lorcaserin) in water has been determined on the basis of one-bond and long-range CH residual dipolar coupling (RDC) data along with DFT computations and 3JHH coupling-constant analysis. According to this analysis, lorcaserin exists as a conformational equilibrium of two crown-chair forms, of which the preferred conformation has the methyl group in an equatorial orientation.