Helv. Chim. Acta 97, 471-490 (2014)

DOI: 10.1002/hlca.201300395

A Spectroscopic Study of Colchicine in the Solid State and in Solution by Multinuclear Magnetic Resonance and Vibrational Circular Dichroism

Although almost 200-years-old, several unknown aspects remain to be explored of colchicine, the unique available drug for acute flares of gout. In this article, we report density-functional theory (DFT) studies of geometry, energy, and NMR; 1H-, 13C-, and 15N-NMR chemical shifts and some spin-spin coupling constants, including the complete analysis of the saturated part (ring B); the assignment of both enantiomers by NMR using a chiral solvating agent; solid-state NMR experiments of the different forms of natural and racemic colchicine, and IR and vibrational circular dichroism (VCD) studies of these same forms.