Metabolite markers for three synthetic tryptamines <i>N</i>‐ethyl‐<i>N</i>‐propyltryptamine, 4‐hydroxy‐<i>N</i>‐ethyl‐<i>N</i>‐propyltryptamine, and 5‐methoxy‐<i>N</i>‐ethyl‐<i>N</i>‐propyltryptamine
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Author (Corporation)
Publication date
2024
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01A - Journal article
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Drug Testing and Analysis
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Volume
16
Issue / Number
12
Pages / Duration
1544-1557
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Publisher / Publishing institution
Wiley
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Abstract
N-Ethyl-N-propyltryptamine (EPT), 4-hydroxy-N-ethyl-N-propyltryptamine (4-OH-EPT), and 5-methoxy-N-ethyl-N-propyltryptamine (5-MeO-EPT) are new psychoactive substances classified as tryptamines, sold online. Many tryptamines metabolize rapidly, and identifying the appropriate metabolites to reveal intake is essential. While the metabolism of 4-OH-EPT and 5-MeO-EPT are not previously described, EPT is known to form metabolites by indole ring hydroxylation among others. Based on general knowledge of metabolic patterns, 5-MeO-EPT is also expected to form ring hydroxylated EPT (5-OH-EPT). In the present study, the aim was to characterize the major metabolites of EPT, 4-OH-EPT, and 5-MeO-EPT, to provide markers for substance identification in forensic casework. The tryptamines were incubated with pooled human liver microsomes at 37°C for up to 4 h. The generated metabolites were separated and detected by ultra-high performance liquid chromatography–quadrupole time-of-flight mass spectrometry analysis. The major in vitro EPT metabolites were formed by hydroxylation, N-dealkylation, and carbonylation. In comparison, 4-OH-EPT metabolism was dominated by double bond formation, N-dealkylation, hydroxylation, and carbonylation in vitro and hydroxylation or carbonylation combined with double bond loss, carbonylation, N-dealkylation, and hydroxylation in vivo. 5-MeO-EPT was metabolized by O-demethylation, hydroxylation, and N-dealkylation in vitro. The usefulness of the characterized metabolites in forensic casework was demonstrated by identification of unique metabolites for 4-OH-EPT in a human postmortem blood sample with suspected EPT or 4-OH-EPT intoxication.
Keywords
4-hydroxy-N-ethyl-N-propyltryptamine (4-OH-EPT), Ultra-high performance liquid chromatography–quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS), Synthetic tryptamines, New psychoactive substances (NPS), N-ethyl-N-propyltryptamine (EPT), Metabolite, 5-methoxy-N-ethyl-N-propyltryptamine (5-MeO-EPT), Microsomes
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ISBN
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1942-7603
1942-7611
1942-7611
Language
English
Created during FHNW affiliation
Yes
Strategic action fields FHNW
Publication status
Published
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Peer review of the complete publication
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Hybrid
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Citation
Bergh, M. S.-S., Bogen, I. L., Grafinger, K., Huestis, M. A., & Øiestad, Å. M. L. (2024). Metabolite markers for three synthetic tryptamines <i>N</i>‐ethyl‐<i>N</i>‐propyltryptamine, 4‐hydroxy‐<i>N</i>‐ethyl‐<i>N</i>‐propyltryptamine, and 5‐methoxy‐<i>N</i>‐ethyl‐<i>N</i>‐propyltryptamine. Drug Testing and Analysis, 16(12), 1544–1557. https://doi.org/10.1002/dta.3668