Strategies for the capillary electrophoretic separation of indole alkaloids in Psilocybe semilanceata

Abstract

While the hallucinogenic mushrooms Psilocybe semilanceata have previously been analyzed for the indole alkaloids psilocybin and baeocystin by capillary zone electrophoresis (CZE) at pH 11.5, the present work focused on the development of an alternative and complementary capillary electrophoretic method for their identification. Owing to their structural similarity and zwitterionic nature, the compounds were difficult to resolve based on different interactions with cationic or anionic micelles. However, while the attempts with micellar electrokinetic chromatography (MEKC) were unsuccessful, rapid derivatization with propyl chloroformate and reanalysis by CZE at pH 11.5 was effective to support identification of the two indole alkaloids. Psilocin was difficult to analyze by CZE at pH 11.5 owing to comigration with the electroosmotic flow. For this compound, the pH of the running buffer was reduced to 7.2 to effectively enhance the electrophoretic mobility.

Fungal Hallucinogens Psilocin, Ibotenic Acid, and Muscimol

“…95 Capillary zone electrophoresis was also used for detection of psilocybin/psilocin and other indole compounds. 55,97,118,119 A new method was developed for the screening of urine samples for the presence of 19 drugs of abuse including psilocin. 106 The addition of b-cyclodextrin and organic solvents to the background electrolyte made possible selective separation of analytes.…”

Occurrence and use of hallucinogenic mushrooms containing psilocybin alkaloids

“…P. Kumm., Norway, n=1 capillary zone electrophoresis 10 400-10 500 Pedersen-Bjergaard et al, 1998 Psilocybe semilanceata (Fr.) P.…”

Capillary electrophoresis at the omics level: Towards systems biology

“…A multiplexed capillary with UV detection is quite suitable for high-throughput analysis in pharmaceutical studies. Amphetamines [155], benzodiazepines [156], bufotenine, psilocybin and related indole alkaloids [157], clenbuterol (chiral analysis with added CDs) [158], cocaine [159], codeine pharmaceuticals [160], g-hydroxybutyrate [161], prion protein [162], and serum procainamide [163] are a few examples of the important drugs which have been detected by CE. Pharmacokinetic studies require sensitive and quantitative analyses that can be used in systems-based representations of medical systems, as can be seen in the review published by Lin et al [164].…”