Isolation of a Potent Naturally Occurring Hallucinogen, Salvinorin A, from Salvia divinorum and Investigation of Its Photo-degradation

Abstract

Salvinorin A, which is present in the natural plant Salvia divinorum, is a unique non-nitrogenous compound with hallucinogenic activity. When salvinorin A isolated from leaves of Salvia divinorum was irradiated with 300 nm UV light in ethyl acetate, it degraded from 100 μg/mL to 2.84 ± 0.05 μg/mL in 30 min. The calculated average rate constant k of this degradation was 0.12/min and the half-life was 5.7 min. When authentic salvinorin A was irradiated by UV light in an organic solution or an aqueous solution, it degraded over 90% within 40 min, whereas when it was irradiated by natural sunlight, it took 8 h to degrade 50% both in an organic and an aqueous solution. Three photodegradation products were tentatively identified by gas chromatography/mass spectrometry. Their structures were similar to that of salvinorin A, suggesting that they are also candidate non-nitrogenous hallucinogens.