Cathinones derivatives‐related deaths as exemplified by two fatal cases involving methcathinone with 4‐methylmethcathinone and 4‐methylethcathinone

Rojek, Sebastian; Kłys, Małgorzata; Maciów-Głąb, Martyna; Kula, Karol; Strona, Marcin

doi:10.1002/dta.1615

Cited by 36 publications

(20 citation statements)

References 19 publications

(54 reference statements)

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“…In the second and third cases, another NPS was also detected and identified as pentedrone belonging to the class of synthetic cathinones. ne normy laboratoryjnej ISO/IEC 17025 dla metod analitycznych i zostały szczegółowo przedstawione we wcześniejszych pracach autorów [10][11][12].…”

Section: Resultsunclassified

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

Rojek¹,

Korczyńska-Albert²,

Kulikowska³

et al. 2017

amsik

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Section: Resultsunclassified

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

Rojek¹,

Korczyńska-Albert²,

Kulikowska³

et al. 2017

amsik

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“…Exposure to NPS can result in significant health risks as demonstrated by frequent reports on toxic effects and fatal intoxications. [3][4][5][6][7] Therefore, clinical and forensic toxicologists should be able to reliably detect an intake of NPS. Both parent compounds and metabolites can be suitable screening targets in human biosamples, which are especially important for the development of urine screening approaches.…”

Section: Introductionmentioning

confidence: 99%

Phenethylamine‐derived new psychoactive substances 2C‐E‐FLY, 2C‐EF‐FLY, and 2C‐T‐7‐FLY: Investigations on their metabolic fate including isoenzyme activities and their toxicological detectability in urine screenings

Wagmann

Hempel

Richter

et al. 2019

Drug Testing and Analysis

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Psychoactive substances of the 2C‐series are phenethylamine‐based designer drugs that can induce psychostimulant and hallucinogenic effects. The so‐called 2C‐FLY series contains rigidified methoxy groups integrated in a 2,3,6,7‐tetrahydrobenzo[1,2‐b:4,5‐b']difuran core. The aim of the presented work was to investigate the in vivo and in vitro metabolic fate including isoenzyme activities and toxicological detectability of the three new psychoactive substances (NPS) 2C‐E‐FLY, 2C‐EF‐FLY, and 2C‐T‐7‐FLY to allow clinical and forensic toxicologists the identification of these novel compounds. Rat urine, after oral administration, and pooled human liver S9 fraction (pS9) incubations were analyzed by liquid chromatography−high‐resolution tandem mass spectrometry (LC−HRMS/MS). By performing activity screenings, the human isoenzymes involved were identified and toxicological detectability in rat urine investigated using standard urine screening approaches (SUSAs) based on gas chromatography (GC)−MS, LC−MSn, and LC−HRMS/MS. In total, 32 metabolites were tentatively identified. Main metabolic steps consisted of hydroxylation and N‐acetylation. Phase I metabolic reactions were catalyzed by CYP2D6, 3A4, and FMO3 and N‐acetylation by NAT1 and NAT2. Methoxyamine was used as a trapping agent for detection of the deaminated metabolite formed by MAO‐A and B. Interindividual differences in the metabolism of the 2C‐FLY drugs could be caused by polymorphisms of enzymes involved or drug–drug interactions. All three SUSAs were shown to be suitable to detect an intake of these NPS but common metabolites of 2C‐E‐FLY and 2C‐EF‐FLY have to be considered during interpretation of analytical findings.

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“…[5] In the early 2000s, synthetic cathinones emerged on the recreational drug market as legal alternatives ('legal highs') to amphetamine, Ecstasy, or cocaine. [7][8][9] The cathinone backbone can be modified in three different places to create hundreds of possible compounds, which include substituents on the aromatic ring, the alpha carbon, and the amine group. [7][8][9] The cathinone backbone can be modified in three different places to create hundreds of possible compounds, which include substituents on the aromatic ring, the alpha carbon, and the amine group.…”

Section: Introductionmentioning

confidence: 99%

Identification and analytical characterization of nine synthetic cathinone derivatives N‐ethylhexedrone, 4‐Cl‐pentedrone, 4‐Cl‐α‐EAPP, propylone, N‐ethylnorpentylone, 6‐MeO‐bk‐MDMA, α‐PiHP, 4‐Cl‐α‐PHP, and 4‐F‐α‐PHP

Liu

Wang

et al. 2016

Drug Testing and Analysis

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Clinical and forensic toxicology laboratories are continuously confronted by analytical challenges when dealing with the new psychoactive substances (NPS) phenomenon. In this study, the analytical characterization of nine synthetic cathinones is described: 2-(ethylamino)-1-phenylhexan-1-one (N-ethylhexedrone 1), 1-(4-chlorophenyl)-2-(methylamino)pentan-1-one (4-Cl-pentedrone 2), 1-(4-chlorophenyl)-2-(ethylamino)pentan-1-one (4-Cl-α-EAPP 3), 1-(3,4-methylenedioxyphenyl)-2-propylaminopropan-1-one (propylone 4), 1-(3,4-methylenedioxyphenyl)-2-ethylaminopentan-1-one (N-ethylnorpentylone 5), 1-(6-methoxy-3,4-methylenedioxyphenyl)-2-methylaminopropan-1-one (6-MeO-bk-MDMA 6), 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one (α-PiHP 7), 1-(4-chlorophenyl)-2-(pyrrolidin-1-yl)hexan-1-one (4-Cl-α-PHP 8), and 1-(4-fluorophenyl)-2-(pyrrolidin-1-yl)hexan-1-one (4-F-α-PHP 9). The identification was based on ultra-high-performance liquid chromatography-quadrupole time-of-flight-mass spectrometry (UHPLC-QTOF-MS), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) spectroscopy. The mass-spectral fragmentations of these compounds following collision-induced dissociation (CID) and electron ionization (EI) were studied to assist forensic laboratories in identifying these compounds or other substances with similar structure in their case work. To our knowledge, no analytical data about the compounds 1-4, 7, and 8 have appeared until now, making this the first report on these compounds. The GC-MS data of 5, 6 and 9 has been reported, but this study added the LC-MS, Fourier Transform Infrared (FTIR) and NMR data for additional characterization. Copyright © 2016 John Wiley & Sons, Ltd.

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Cathinones derivatives‐related deaths as exemplified by two fatal cases involving methcathinone with 4‐methylmethcathinone and 4‐methylethcathinone

Cited by 36 publications

References 19 publications

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

Phenethylamine‐derived new psychoactive substances 2C‐E‐FLY, 2C‐EF‐FLY, and 2C‐T‐7‐FLY: Investigations on their metabolic fate including isoenzyme activities and their toxicological detectability in urine screenings

Identification and analytical characterization of nine synthetic cathinone derivatives N‐ethylhexedrone, 4‐Cl‐pentedrone, 4‐Cl‐α‐EAPP, propylone, N‐ethylnorpentylone, 6‐MeO‐bk‐MDMA, α‐PiHP, 4‐Cl‐α‐PHP, and 4‐F‐α‐PHP

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