The bioactivity of 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and its detection in rat urine by capillary electrophoresis combined with an on-line sample concentration technique

Chiu, Yu Chih; Chou, Shiu Huey; Liu, Ju Tsung; Lin, Cheng Huang

doi:10.1016/j.jchromb.2004.08.021

Cited by 13 publications

(2 citation statements)

References 22 publications

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“…Many analytical methods, such as gas chromatography (Matsumoto et al ., ), capillary electrophoresis (Chiu et al ., ), thin‐layer chromatography (Doi et al ., ), gas chromatography–mass spectrometry (GC/MS; Frison et al ., ; Theobald et al ., ; Kikura‐Hanajiri et al ., ), liquid chromatography (LC) with chemiluminescence (Nakamura et al ., ) or fluorescence detection (Tomita et al ., ; Min et al ., ), LC with electrochemical detection (Min et al ., ) and LC/MS (Inagaki et al ., , ) for illicit drugs have been reported. Many of these methods have successfully been used to determine various illicit drugs in products.…”

Section: Introductionmentioning

confidence: 99%

UPLC/ESI‐MS/MS‐based determination of metabolism of several new illicit drugs, ADB‐FUBINACA, AB‐FUBINACA, AB‐PINACA, QUPIC, 5F‐QUPIC and α‐PVT, by human liver microsome

Takayama

Suzuki

Todoroki

et al. 2014

Biomedical Chromatography

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The metabolism by human liver microsomes of several new illicit drugs, that is, N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3- carboxamide (ADB-FUBINACA), N-(1-amino-3-methyl-1-oxobutan-2-yl)-1- (4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA), N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA), quinolin-8-yl 1-pentyl-(1H-indole)-3-carboxylate (QUPIC), quinolin-8-yl 1-(5-fluoropentyl)-(1H-indole)-3-carboxylate (5 F-QUPIC) and α-pyrrolidinovalerothiophenone (α-PVT), which have indole, indazole, quinolinol ester and thiophene structures, was investigated using reversed-phase chromatography and mass spectrometry. The present method is based upon the oxidation by cytochrome p450 superfamily enzymes in the microsomes. The oxidation of ADB-FUBINACA and AB-FUBINACA mainly occurred on the N-(1-amino-alkyl-1-oxobutan) moiety. However, the oxidation of AB-PINACA seemed to occur on the 1-pentyl moiety. On the other hand, QUPIC and 5 F-QUPIC, which have a quinolinol ester structure, predominantly underwent a cleavage reaction to produce indoleacetic acid type metabolites. In contrast, the metabolism reaction of α-PVT was different from that of the other tested drugs, and various oxidation products were observed on the chromatograms. The obtained metabolites are not in conflict with the results predicted by MetaboLynx software. However, the exact structures of the metabolites, except for 1-pentyl-1H-indole-3-carboxylic acid (QUPIC metabolite) and 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid (5 F-QUPIC metabolite), are currently not proven, because we have no authentic compounds for comparison. The proposed approach using human liver microsome seems to provide a new technology for the prediction of possible metabolites occuring in humans.

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Section: Introductionmentioning

confidence: 99%

UPLC/ESI‐MS/MS‐based determination of metabolism of several new illicit drugs, ADB‐FUBINACA, AB‐FUBINACA, AB‐PINACA, QUPIC, 5F‐QUPIC and α‐PVT, by human liver microsome

Takayama

Suzuki

Todoroki

et al. 2014

Biomedical Chromatography

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“…2C‐B (4‐bromo‐2,5‐dimethoxy‐β‐phenethylamine) was a first compound of the 2C‐series, marketed in the mid‐1980s, which was sold as an aphrodisiac in Germany and the Netherlands . In the 1990s, S‐alkyl compounds, namely, 2C‐T‐2 (4‐ethylthio‐2,5‐dimethoxy‐β‐phenethylamine) and 2C‐T‐7 (2,5‐dimethoxy‐4‐propylthio‐β‐phenethylamine), as well as iodine analogue, 2C‐I (4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine), appeared on the illegal drug market, leading to several fatal intoxications . Because of increasing problems with the 2Cs, after an official risk assessment prepared by the EMCDDA, many of them were banned in most countries .…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of 2,5‐dimethoxy‐3,4‐dimethyl‐β‐phenethylamine (2C‐G) – A new designer drug

Zuba

Sekuła

2012

Drug Testing and Analysis

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This study presents and discusses the mass spectrometric, infrared spectroscopic and nuclear magnetic resonance spectroscopic data of 2,5-dimethoxy-3,4-dimethyl-β-phenethylamine (2C-G), a new designer drug. A powder sample containing 2C-G was seized in Poland in 2011. The paper focuses on a comparison of the analytical features of 2C-G and other members of the 2C-series, in order to assess the possibility of unequivocal identification. The occurrence of intense peak at m/z = 178 and different intensities of the ions at m/z = 165 and 180 in the gas chromatography-electron impact-mass spectrometry (GC-EI/MS) spectrum of 2C-G made it possible to distinguish it from 2C-E. Differences in relative intensities of the ions at m/z = 192, 179 and 177 were observed for GC-EI/MS spectra of TFAA derivatives of 2C-G and 2C-E. An identical set of ions was recorded for these substances using the liquid chromatography-electrospray ionization/quadrupole time of flight mass spectrometry (LC-ESI/QTOFMS) method in both MS and tandem mass spectrometry (MS/MS) mode, but the distinction was possible based on differences in the ion intensities at m/z = 193.1223 and 178.0988. The Fourier transform infrared (FTIR) spectrum of 2C-G was significantly different from other members of the 2C-series, with a characteristic doublets at 993-1014 cm(-1) and 1099-1124 cm(-1) , and the ratio of bands at higher wavenumbers. Final elucidation of the structure of 2C-G was carried out by (1) H and (13) C NMR spectroscopy. The study indicated that the marketing of analogues of controlled substances poses a real analytical challenge for forensic laboratories, and the application of sophisticated methods is often required for unequivocal identification of a new substance.

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Contemporary sample stacking in CE: A sophisticated tool based on simple principles

et al. 2007

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Sample stacking is a general term for methods in CE which are used for on-line concentration of diluted analytes. During the stacking process, analytes present at low concentrations in a long injected sample zone are concentrated into a short zone (stack). The stacked analytes are then separated and individual zones are detected. Thus stacking provides better separation efficiency and detection sensitivity. Many papers have been published on stacking till now, various procedures have been described, and, many names have been proposed for stacking procedures utilizing the same principles. This contribution brings an easy and unified view on stacking, describes the basic principles utilized, makes a list of recognized operational principles and brings an overview of principal current procedures. Further, it surveys selected recent practical applications ordered according to their operational principles and includes the terms, nicknames, and acronyms used for these actual stacking procedures. This contribution may help both newcomers and experts in the field of CE to orient themselves in the already quite complex topic of sample stacking.

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The bioactivity of 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and its detection in rat urine by capillary electrophoresis combined with an on-line sample concentration technique

Cited by 13 publications

References 22 publications

UPLC/ESI‐MS/MS‐based determination of metabolism of several new illicit drugs, ADB‐FUBINACA, AB‐FUBINACA, AB‐PINACA, QUPIC, 5F‐QUPIC and α‐PVT, by human liver microsome

UPLC/ESI‐MS/MS‐based determination of metabolism of several new illicit drugs, ADB‐FUBINACA, AB‐FUBINACA, AB‐PINACA, QUPIC, 5F‐QUPIC and α‐PVT, by human liver microsome

Identification and characterization of 2,5‐dimethoxy‐3,4‐dimethyl‐β‐phenethylamine (2C‐G) – A new designer drug

Contemporary sample stacking in CE: A sophisticated tool based on simple principles

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