Spectroscopic behavior of bufotenine and bufotenine N-oxide: Solvent and pH effects and interaction with biomembrane models.

Bufotenine and bufotenine N-oxide, two fluorescent analogs of the psychedelic compound DMT, show changes in their light absorption and emission depending on the acidity (pH) and the type of solvent they are in. In experiments with models of biological membranes, such as micelles and liposomes, both molecules interact with pre-micellar structures and with micelles, as indicated by shifts in their fluorescence spectra. Steady-state anisotropy measurements reveal that both molecules associate with liposomes without altering the fluidity of the lipid bilayer. These spectroscopic properties may aid in designing new pharmacologically active compounds inspired by bufotenine and in using these molecules as markers for psychiatric disorders.

Study at a glance

Abstract

Bufotenine is a fluorescent analog of Dimethyltryptamine (DMT) that has been widely studied due to its psychedelic properties and biological activity. However, little is known about its spectroscopic properties in different media. Thus, we present in this work, for the first time, the spectroscopic behavior of bufotenine and bufotenine N-oxide by means of their fluorescence properties. Both molecules exhibit changes in optical absorption and emission spectra with variations in pH of the medium and in different solvents. Assays in the presence of biomembranes models, like micelles and liposomes, were also performed. In surfactants titration experiments, the spectral shift observed in fluorescence shows the interaction of both molecules with pre-micellar structures and with micelles. Steady state anisotropy measurements show that both bufotenine and bufotenine N-oxide, in the studied concentration range, interact with liposomes without causing changes in the fluidity of the lipid bilayer. These results can be useful in studies that aim at searching for new compounds, inspired by bufotenine and bufotenine N-oxide, with relevant pharmacological activities and also in studies that use these molecules as markers of psychiatric disorders.