ACS Omega
April 1, 2022
Luisina Castelli Rodríguez, Andrés Mariño López, Guillermo Moyna et al.
28 citations
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.
Journal of natural products
June 23, 2023
Bruno González, Nicolás Veiga, Gonzalo Hernández et al.
7 citations
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.
Journal of psychoactive drugs
January 1, 2023
Ismael Apud, Juan Scuro, Luisina Rodríguez et al.
4 citations
People who use ayahuasca in a neo-shamanic group and a Santo Daime church in Uruguay differ in personality and acute psychological effects. Santo Daime members scored lower on Neuroticism-Anxiety, Dependence, Low Self-Esteem, Anger, and Restlessness, possibly due to the protective effects of a structured church religion or because some neo-shamanic participants were undergoing treatment. During rituals, the neo-shamanic group reported stronger somesthesia and perception, linked to their high-arousal setting. Chemical analysis found typical alkaloids with no adulterants; the neo-shamanic sample had a higher β-carbolines-to-DMT ratio, which may explain the stronger somesthetic effects. Personality and acute effects correlated only in the neo-shamanic group, suggesting a more individualistic tradition.