Investigating the ability of the microbial model Cunninghamella elegans for the metabolism of synthetic tryptamines.

Grafinger, Katharina; Wilke, Andreas; König, Stefan; Weinmann, Wolfgang (2019). Investigating the ability of the microbial model Cunninghamella elegans for the metabolism of synthetic tryptamines. Drug testing and analysis, 11(5), pp. 721-729. Wiley 10.1002/dta.2544

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Tryptamines can occur naturally in plants, mushrooms, microbes and amphibians and synthetic tryptamines have been sold as New Psychoactive Substances (NPS), due to their hallucinogenic effects. When it comes to NPS, metabolism studies are of crucial importance, due to the lack of pharmacological and toxicological data. In order to study in vitro and in vivo metabolism of xenobiotica, different approaches can be taken. The zygomycete fungus Cunninghamella elegans (C. elegans) can be used as a microbial model for the study of drug metabolism. The current study investigated the biotransformation of four natural occurring and synthetic tryptamines (N,N-Dimethyltryptamine (DMT), 4-hydroxy-N-methyl-N-ethyltryptamine (4-HO-MET), N,N-di allyl-5-methoxy tryptamine (5-MeO-DALT) and 5-methoxy-N-methyl-N-isoporpoyltryptamine (5-MeO-MiPT)) in C. elegans after incubation for 72 hours. Metabolites were identified using liquid chromatography-high resolution-tandem mass spectrometry (LC-HR-MS/MS) with a quadrupole time-of-flight (QqToF) instrument. Results were compared to already published data on these substances. C. elegans was capable to produce all major biotransformation steps, hydroxylation, N-oxide formation, carboxylation, deamination and demethylation. On average 63 % of phase I metabolites found in literature could also be detected in C. elegans. Additionally, metabolites specific for C. elegans were identified. Therefore, C. elegans is a suitable complementary model to other in vitro or in vivo methods to study the metabolism of naturally occurring or synthetic tryptamines.

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