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
Lade...
Autor:in (Körperschaft)
Publikationsdatum
2024
Typ der Arbeit
Studiengang
Typ
01A - Beitrag in wissenschaftlicher Zeitschrift
Herausgeber:innen
Herausgeber:in (Körperschaft)
Betreuer:in
Übergeordnetes Werk
Drug Testing and Analysis
Themenheft
DOI der Originalpublikation
Link
Reihe / Serie
Reihennummer
Jahrgang / Band
16
Ausgabe / Nummer
12
Seiten / Dauer
1544-1557
Patentnummer
Verlag / Herausgebende Institution
Wiley
Verlagsort / Veranstaltungsort
Auflage
Version
Programmiersprache
Abtretungsempfänger:in
Praxispartner:in/Auftraggeber:in
Zusammenfassung
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.
Schlagwörter
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
Fachgebiet (DDC)
Veranstaltung
Startdatum der Ausstellung
Enddatum der Ausstellung
Startdatum der Konferenz
Enddatum der Konferenz
Datum der letzten Prüfung
ISBN
ISSN
1942-7603
1942-7611
1942-7611
Sprache
Englisch
Während FHNW Zugehörigkeit erstellt
Ja
Zukunftsfelder FHNW
Publikationsstatus
Veröffentlicht
Begutachtung
Peer-Review der ganzen Publikation
Open Access-Status
Hybrid
Lizenz
Zitation
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