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, Julian A.; Helfer, Andreas G.; Brandt, Simon D.; Meyer, Markus R.; Maurer, Hans H.

doi:10.1007/s00216-015-8955-0

Cited by 45 publications

(56 citation statements)

References 28 publications

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“…As described previously [9,19], 500 µL of acetonitrile was added to 100 µL of urine. The mixture was shaken on a rotary shaker for 2 min.…”

Section: Sample Preparation For Identification Of Phase I and Ii Metamentioning

confidence: 99%

“…Conditions for performing the microsomal incubations were published previously [9,20]. Briefly, compounds (50 µmol/L each) were incubated with the CYP isoenzymes (50 pmol/mL, each) CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1, CYP3A4, CYP3A5, or pHLM (1 mg protein/mL) for 30 min.…”

Section: Microsomal Incubations For Phlm and Initial Cyp Activity Scrmentioning

confidence: 99%

“…[5,6]. N,N-Diallyltryptamine (DALT) derivatives represent an important group with 5-methoxy-DALT (5-MeO-DALT) being the most often reported example [7][8][9]. As such drugs may become controlled the creation of new substances with similar chemical structures and effects is aimed at circumventing legislative restrictions [5], which leads to significant challenges for drug testing laboratories in the attempt to be kept up-to-date with analytical methods and reference data [10,11].…”

Section: Introductionmentioning

confidence: 99%

“…In a previous study, DALT and 5-MeO-DALT were investigated in detail concerning metabolism and urinalysis [9]. The present study describes the biotransformation and detectability of three ring substituted DALT derivatives 5-fluoro-DALT (5-F-DALT), 7-methyl-DALT (7-Me-DALT), and 5,6-methylenedioxy-DALT (5,6-MD-DALT), which were synthesized in advance of potential distribution as NPS [12].…”

Section: Introductionmentioning

confidence: 99%

“…Investigations were performed as usual [9] with rat urine samples taken from male Wistar rats (Charles River, Sulzfeld, Germany) for toxicological diagnostic reasons. The test drugs were administered once in an aqueous suspension by gastric intubation in a single 20 mg/kg body mass (BM) dose for the identification of the metabolites and once in a single 1 or 0.1 mg/kg BM dose for toxicological analysis according to the German animal protection act.…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation and detectability of the new psychoactive substances N,N-diallyltryptamine (DALT) derivatives 5-fluoro-DALT, 7-methyl-DALT, and 5,6-methylenedioxy-DALT in urine using GC-MS, LC-MSn, and LC-HR-MS/MS

et al. 2016

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Derivatives of N,N-diallyltryptamine (DALT) can be classified as new psychoactive substances. Biotransformation and detectability of 5-fluoro-DALT (5-F-DALT), 7-methyl-DALT (7-Me-DALT), and 5,6-methylenedioxy-DALT (5,6-MD-DALT) are described here. Their metabolites detected in rat urine and pooled human liver microsomes were identified by liquid chromatography (LC)-high resolution (HR)-tandem mass spectrometry (MS/MS). In addition, the human cytochrome-P450 (CYP) isoenzymes involved in the main metabolic steps were identified and detectability tested in urine by the authors' urine screening approaches using GC-MS, LC-MS n ,or LC-HR-MS/MS. Aromatic and aliphatic hydroxylations, N-dealkylation, N-oxidation, and combinations could be proposed for all compounds as main pathways. Carboxylation after initial hydroxylation of the methyl group could also be detected for 7-Me-DALT and O-demethylenation was observed for 5,6-MD-DALT. All phase I metabolites were extensively glucuronidated or sulfated. Initial phase I reactions were catalyzed by CYP1A2, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP3A4, and CYP3A5. Rat urine samples were analyzed following two different low dose administrations. GC-MS was not able to monitor consumption reliably, but all three drugs are predicted to be detectable in cases of overdose. The LC-MS n and LC-HR-MS/MS approaches were suitable for detect an intake of all three compounds mainly via their metabolites. However, after the lowest dose, a reliable monitoring could only be achieved for 5-F-DALT via LC-MS n and LC-HR-MS/MS and for 7-Me-DALT via LC-HR-MS/MS. The most abundant targets in both LC-MS screenings were one of two hydroxy-aryl metabolites and both corresponding glucuronides for 5-F-DALT, one N-deallyl hydroxy-aryl, the carboxy, and one dihydroxy-aryl metabolite for 7-Me-DALT, and the demethylenyl metabolite, its oxo metabolite, and glucuronide for 5,6-MD-DALT.

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“…As described previously [9,19], 500 µL of acetonitrile was added to 100 µL of urine. The mixture was shaken on a rotary shaker for 2 min.…”

Section: Sample Preparation For Identification Of Phase I and Ii Metamentioning

confidence: 99%

Section: Microsomal Incubations For Phlm and Initial Cyp Activity Scrmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biotransformation and detectability of the new psychoactive substances N,N-diallyltryptamine (DALT) derivatives 5-fluoro-DALT, 7-methyl-DALT, and 5,6-methylenedioxy-DALT in urine using GC-MS, LC-MSn, and LC-HR-MS/MS

et al. 2016

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Analytical characterization of N,N‐diallyltryptamine (DALT) and 16 ring‐substituted derivatives

Brandt

Kavanagh

Dowling

et al. 2016

Drug Testing and Analysis

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Many N,N-dialkylated tryptamines show psychoactive properties in humans and the number of derivatives involved in multidisciplinary areas of research has grown over the last few decades. Whereas some derivatives form the basis of a range of medicinal products, others are predominantly encountered as recreational drugs, and in some cases, the areas of therapeutic and recreational use can overlap. In recent years, 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT) has appeared as a new psychoactive substance (NPS) and ‘research chemical’ whereas 4-acetoxy-DALT and the ring-unsubstituted DALT have only been detected very recently. Strategies pursued in the authors’ laboratories included the preparation and biological evaluation of previously unreported N,N-diallyltryptamines (DALTs). This report describes the analytical characterization of seventeen DALTs. Fifteen DALTs were prepared by a microwave-accelerated Speeter and Anthony procedure following established procedures developed previously in the authors’ laboratories. In addition to DALT, the substances included in this study were 2-phenyl-, 4-acetoxy-, 4-hydroxy-, 4,5-ethylenedioxy-, 5-methyl-, 5-methoxy-, 5-methoxy-2-methyl-, 5-ethoxy-, 5-fluoro-, 5-fluoro-2-methyl-, 5-chloro-, 5-bromo-, 5,6-methylenedioxy-, 6-fluoro-, 7-methyl, and 7-ethyl-DALT, respectively. The DALTs were characterized by nuclear magnetic resonance spectroscopy (NMR), gas chromatography (GC) quadrupole and ion trap (EI/CI) mass spectrometry (MS), low and high mass accuracy MS/MS, ultraviolet diode array detection and GC solid-state infrared analysis, respectively. A comprehensive collection of spectral data was obtained that are provided to research communities who face the challenge of encountering newly emerging substances where analytical data are not available. These data are also relevant to researchers who might wish to explore the clinical and non-clinical uses of these substances.

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Microbial biotransformation of five pyrrolidinophenone‐type psychoactive substances in wastewater and a wastewater isolated Pseudomonas putida strain

Mardal

Bischoff

Ibáñez

et al. 2017

Drug Testing and Analysis

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Wastewater-based epidemiology (WBE) employs the analysis of wastewater to detect and quantify drug use and discharge within a community. In this work, transformation products (TP) by microbes in the environment were identified after incubations in wastewater and an isolated microbial strain. The microbial strain was isolated from an enrichment culture of wastewater supplemented with 3,4-methylenedioxy-pyrovalerone, and identified by matrix assisted laser desorption - time of flight mass spectrometry as Pseudomonas putida (P. putida). Five pyrrolidinophenone-type psychoactive substances (PPPS) were then incubated in wastewater and in P. putida tryptic soy broth (TSB) growth cultures. TPs were identified using liquid chromatography coupled to mass spectrometry techniques. All TPs observed in P. putida TSB growth cultures were also identified in wastewater incubations. The main TP for all PPPSs in P. putida TSB growth cultures, and two PPPSs incubated in wastewater, were the N-desalkyl-carboxy-TPs. The study showed P. putida TSB growth cultures used for identification of TPs in wastewater, represent parts of the microbial community. With data provided in this type of experiments more information will be available to select targets for monitoring drug use by WBE. Copyright © 2017 John Wiley & Sons, Ltd.

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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

Cited by 45 publications

References 28 publications

Biotransformation and detectability of the new psychoactive substances N,N-diallyltryptamine (DALT) derivatives 5-fluoro-DALT, 7-methyl-DALT, and 5,6-methylenedioxy-DALT in urine using GC-MS, LC-MSn, and LC-HR-MS/MS

Biotransformation and detectability of the new psychoactive substances N,N-diallyltryptamine (DALT) derivatives 5-fluoro-DALT, 7-methyl-DALT, and 5,6-methylenedioxy-DALT in urine using GC-MS, LC-MSn, and LC-HR-MS/MS

Analytical characterization of N,N‐diallyltryptamine (DALT) and 16 ring‐substituted derivatives

Microbial biotransformation of five pyrrolidinophenone‐type psychoactive substances in wastewater and a wastewater isolated Pseudomonas putida strain

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