Laboratorio de Resonancia Magnética Nuclear, Departamento de Química Orgánica, Facultad de Química, Universidad de la República, 11800 Montevideo, Uruguay.
2 papers in the library · 35 citations · publishing 2022-2023
Ayahuasca, a psychedelic beverage from the Amazon, is made by boiling Banisteriopsis caapi vine with DMT-containing plants. Using NMR and LC-MS/MS, this study analyzed both soluble and insoluble components of ayahuasca samples. For the first time, fructose was detected as a major component, and the alkaloid harmine was found in suspended solids. The major alkaloids identified were DMT, harmine, tetrahydroharmine, harmaline, and harmol. A new quantitative NMR method was developed and validated to simultaneously quantify these alkaloids.
The iboga alkaloids, such as ibogaine and voacangine, are promising scaffolds for developing drugs to treat neuropsychiatric disorders. This work examines how these molecules react under oxidation with dioxygen, peroxo compounds, and iodine. The C16-carboxymethyl ester group in voacangine makes the molecule more stable toward oxidation than ibogaine, particularly in the indole ring, where 7-hydroxy- or 7-peroxy-indolenines form. However, the ester increases reactivity at the isoquinuclidinic nitrogen, leading to C3-oxidized products via regioselective iminium formation. Density functional theory calculations explain this differential reactivity. Additionally, NMR experiments and theoretical calculations revise the absolute stereochemistry at C7 in voacangine's 7-hydroxyindolenine to S, correcting earlier reports of R configuration.