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Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MS (n) , and LC-HR-MS-MS

Michely, JA and Helfer, AG and Brandt, SD and Meyer, MR and Maurer, HH (2015) Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MS (n) , and LC-HR-MS-MS. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 407 (25). pp. 7831-7842. ISSN 1618-2642

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Abstract

N,N-Diallyltryptamine (DALT) and 5-methoxy-DALT (5-MeO-DALT) are synthetic tryptamine derivatives commonly referred to as so-called new psychoactive substances (NPS). They have psychoactive effects that may be similar to those of other tryptamine derivatives. The objectives of this work were to study the metabolic fate and detectability, in urine, of DALT and 5-MeO-DALT. For metabolism studies, rat urine obtained after high-dose administration was prepared by precipitation and analyzed by liquid chromatography–high-resolution mass spectrometry (LC–HR–MS–MS). On the basis of the metabolites identified, several aromatic and aliphatic hydroxylations, N-dealkylation, N-oxidation, and combinations thereof are proposed as the main metabolic pathways for both compounds. O-Demethylation of 5-MeO-DALT was also observed, in addition to extensive glucuronidation or sulfation of both compounds after phase I transformation. The cytochrome P450 (CYP) isoenzymes predominantly involved in DALT metabolism were CYP2C19, CYP2D6, and CYP3A4; those mainly involved in 5-MeO-DALT metabolism were CYP1A2, CYP2C19, CYP2D6, and CYP3A4. For detectability studies, rat urine was screened by GC–MS, LC–MS n , and LC–HR–MS–MS after administration of low doses. LC–MS n and LC–HR–MS–MS were deemed suitable for monitoring consumption of both compounds. The most abundant targets were a ring hydroxy metabolite of DALT, the N,O-bis-dealkyl metabolite of 5-MeO-DALT, and their glucuronides. GC–MS enabled screening of DALT by use of its main metabolites only.

Item Type: Article
Additional Information: The final publication is available at Springer via http://dx.doi.org/10.1007/s00216-015-8955-0
Uncontrolled Keywords: 03 Chemical Sciences, 06 Biological Sciences, 09 Engineering
Subjects: R Medicine > RM Therapeutics. Pharmacology
R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: SPRINGER HEIDELBERG
Related URLs:
Date Deposited: 11 Apr 2016 13:06
Last Modified: 22 Aug 2016 23:50
DOI or Identification number: 10.1007/s00216-015-8955-0
URI: http://researchonline.ljmu.ac.uk/id/eprint/3406

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