Synthetic cannabinoid 3-benzyl-5-[1-(2-pyrrolidin-1-ylethyl)-1H-indol-3-yl]-1,2,4-oxadiazole. The first detection in illicit market of new psychoactive substances

Шевырин, Вадим А.; Melkozerov, Vladimir; Eltsov, Oleg S.; Shafran, Yuri; Morzherin, Yu. Yu.

doi:10.1016/j.forsciint.2015.12.019

Cited by 21 publications

(27 citation statements)

References 19 publications

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“…[5][6][7] The earliest SC product, "Spice," was a herbal blend laced with psychoactive SCs CP 47,497-C8 (1, Figure 1) and JWH-018 (2). [9][10][11][12] Of particular concern are the seemingly greater toxicities and dependence liabilities of newer SCs. [9][10][11][12] Of particular concern are the seemingly greater toxicities and dependence liabilities of newer SCs.…”

Section: Introductionmentioning

confidence: 99%

“…8 The prohibition of 1 and 2 resulted in the release of newer analogs that were subsequently banned, and this iterative cycle has produced hundreds of SCs with increasing structural diversity. [9][10][11][12] Of particular concern are the seemingly greater toxicities and dependence liabilities of newer SCs. [13][14][15][16] The confirmation of novel SCs by forensic chemists and clinical toxicologists is hindered by the dynamic heterogeneity of SC products, and the latency between tentative SC identification and availability of suitable commercial reference standards.…”

Section: Introductionmentioning

confidence: 99%

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The chemistry and pharmacology of synthetic cannabinoid SDB‐006 and its regioisomeric fluorinated and methoxylated analogs

Banister

Olson

Winchester

et al. 2018

Drug Testing and Analysis

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Synthetic cannabinoids are the largest and most structurally diverse class of new psychoactive substances, with manufacturers often using isomerism to evade detection and circumvent legal restriction. The regioisomeric methoxy- and fluorine-substituted analogs of SDB-006 (N-benzyl-1-pentyl-1H-indole-3-carboxamide) were synthesized and could not be differentiated by gas chromatography-mass spectrometry (GC-MS), but were distinguishable by liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). In a fluorescence-based plate reader membrane potential assay, SDB-006 acted as a potent agonist at human cannabinoid receptors (CB EC = 19 nM). All methoxy- and fluorine-substituted analogs showed reduced potency compared to SDB-006, although the 2-fluorinated analog (EC = 166 nM) was comparable to known synthetic cannabinoid RCS-4 (EC = 146 nM). Using biotelemetry in rats, SDB-006 and RCS-4 evoked comparable reduction in body temperature (~0.7°C at a dose of 10 mg/kg), suggesting lower potency than the recent synthetic cannabinoid AB-CHMINACA (>2°C, 3 mg/kg).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The chemistry and pharmacology of synthetic cannabinoid SDB‐006 and its regioisomeric fluorinated and methoxylated analogs

Banister

Olson

Winchester

et al. 2018

Drug Testing and Analysis

View full text Add to dashboard Cite

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“…There have been several comprehensive CID studies on synthetic cathinones [19][20][21] using HRMS. There has been some literature published on single and multi-analyte characterization of hallucinogenic phenethylamines [22][23][24][25][26][27][28] and synthetic cannabinoids [29][30][31] using this technique; however, there have been no publications on the comprehensive characterization of these classes with explicitly stated rules or guidelines for the detection of novel analogues in a non-targeted screening approach. The aim of this study was to fill this current gap in research and to investigate the CID pathways of 2C-X, DOX and 25X-NBOMe derivatives using high-resolution mass spectrometry (HRMS) to develop a nontargeted strategy for the detection of new emerging analogues.…”

Section: Introductionmentioning

confidence: 99%

Characterization of hallucinogenic phenethylamines using high‐resolution mass spectrometry for non‐targeted screening purposes

Pasin

Cawley

Bidny³

et al. 2017

Drug Testing and Analysis

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Hallucinogenic phenethylamines such as 2,5-dimethoxyphenethylamines (2C-X) and their N-(2-methoxybenzyl) derivatives (25X-NBOMe) have seen an increase in novel analogues in recent years. These rapidly changing analogues make it difficult for laboratories to rely on traditional targeted screening methods to detect unknown new psychoactive substances (NPS). In this study, twelve 2C-X, six 2,5-dimethoxyamphetamines (DOX), and fourteen 25X-NBOMe derivatives, including two deuterated derivatives (2C-B-d and 25I-NBOMe-d ), were analyzed using ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS). Collision-induced dissociation (CID) experiments were performed using collision energies set at 10, 20, and 40 eV. For 2C-X and DOX derivatives, common losses were observed including neutral and radical losses such as NH (17.0265 Da), •CH N (32.0500 Da), C H N (45.0578 Da) and C H N (47.0735 Da). 2C-X derivatives displayed common product ions at m/z 164.0837 ([C H O ] ), 149.0603 ([C H O ] ), and 134.0732 ([C H O] ) while DOX derivatives had common product ions at m/z 178.0994 ([C H O ] ), 163.0754 ([C H O ] ), 147.0804 ([C H O] ), and 135.0810 ([C H O] ). 25X-NBOMe had characteristic product ions at m/z 121.0654 ([C H O] ) and 91.0548 ([C H ] ) with minor common losses corresponding to 2-methylanisole (C H O, 122.0732 Da), 2-methoxybenzylamine (C H NO, 137.0847 Da), and •C H NO (152.1074 Da). Novel analogues of the selected classes can be detected by applying neutral loss filters (NLFs) and extracting the common product ions. Copyright © 2017 John Wiley & Sons, Ltd.

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“…Powders and crystalline solids were largely prepared using solvent extraction or dilution typically with methanol or acetonitrile for MS analyses utilizing LC or GC separation. Schevyrin et al [22][23][24] dissolved smoke mixtures in methanol followed by an additional filtration step with a cellulose membrane. The extraction of blotter papers has been achieved by soaking the paper in methanol for 6 hours [25][26][27].…”

Section: Seized Materials and Purchased Legal Highsmentioning

confidence: 99%

“…Few studies have involved the use of both LC and GC coupled to HRMS. Schevyrin et al [22][23][24] published a series of articles reporting the detection of several SCs for the first time in smoke mixtures from Russia and Belarus using both LC and GC coupled to QTOF-MS. The combination of both chromatography methods was used in lieu of these compounds having spectra in commercial libraries for GC-MS.…”

Section: Conventional Separation Techniques Coupled To Hrmsmentioning

confidence: 99%

Current applications of high-resolution mass spectrometry for the analysis of new psychoactive substances: a critical review

Pasin

Cawley

Bidny³

et al. 2017

Anal Bioanal Chem

112

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The proliferation of new psychoactive substances (NPS) in recent years has resulted in the development of numerous analytical methods for the detection and identification of known and unknown NPS derivatives. High-resolution mass spectrometry (HRMS) has been identified as the method of choice for broad screening of NPS in a wide range of analytical contexts due to its ability to measure accurate masses using data-independent acquisition (DIA) techniques. Additionally, it has shown promise for non-targeted screening strategies that have been developed in order to detect and identify novel analogues without the need for certified reference materials (CRMs) or comprehensive mass spectral libraries. This paper reviews the applications of HRMS for the analysis of NPS in forensic drug chemistry, clinical and forensic toxicology. It provides an overview of the sample preparation procedures in addition to data acquisition, instrumental analysis and data processing techniques.Furthermore, it will give an overview of the current state of non-targeted screening strategies with discussion on future directions and perspectives of this technique.3

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Synthetic cannabinoid 3-benzyl-5-[1-(2-pyrrolidin-1-ylethyl)-1H-indol-3-yl]-1,2,4-oxadiazole. The first detection in illicit market of new psychoactive substances

Cited by 21 publications

References 19 publications

The chemistry and pharmacology of synthetic cannabinoid SDB‐006 and its regioisomeric fluorinated and methoxylated analogs

The chemistry and pharmacology of synthetic cannabinoid SDB‐006 and its regioisomeric fluorinated and methoxylated analogs

Characterization of hallucinogenic phenethylamines using high‐resolution mass spectrometry for non‐targeted screening purposes

Current applications of high-resolution mass spectrometry for the analysis of new psychoactive substances: a critical review

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