Epimerization Studies of LSD Using 1H Nuclear Magnetic Resonance (NMR) Spectroscopy
Journal of Analytical Toxicology October 1, 1997 S. J. Salamone, Z. Li, A. J. Mcnally et al. 23 citations
LSD converts to its epimer iso-LSD at temperatures above 37 °C and pH levels over 7.0. At pH 7.0 or higher, a 9:1 ratio of LSD to iso-LSD is reached after one week at 45 °C or two weeks at 37 °C. Starting from iso-LSD, achieving the same 9:1 ratio requires six weeks at 45 °C and pH 9.7, indicating more vigorous conditions are needed. This ratio represents an equilibrium concentration with an equilibrium constant K = 9. The study used proton NMR to follow the reaction by integrating the C-9 resonances of LSD and iso-LSD, appearing as singlets at 6.35 and 6.27 ppm respectively. This is the first quantitative measurement of LSD epimerization by NMR.