Identification of the novel synthetic cannabimimetic 8-quinolinyl 4-methyl-3-(1-piperidinylsulfonyl)benzoate (QMPSB) and other designer drugs in herbal incense

Blakey, Karen; Boyd, Sue E.; Atkinson, Sarah D.; Wolf, Jenna; Slottje, Pim M.; Goodchild, Katrina; McGowan, Jenny

doi:10.1016/j.forsciint.2015.12.001

Cited by 19 publications

(51 citation statements)

References 19 publications

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“…Assignment of signals was assisted by correlation spectroscopy (COSY), distortionless enhancement by polarization transfer (DEPT), heteronuclear single quantum coherence (HSQC), and heteronuclear multiple bond correlation (HMBC) experiments where necessary. For compounds containing saturated heterocyclic amides (5)(6)(7)(8)(11)(12)(13)(14), severe exchange broadening of the amide αand β-carbon signals was observed, consistent with previous characterization of analogous systems. 40 The total ion chromatogram (TIC) obtained from the LC−QTOF−MS run was analyzed using Agilent MassHunter Qualitative Analysis software.…”

Section: Nmr Spectroscopy Methodssupporting

confidence: 90%

“…As acylindole SCRAs were prohibited in various jurisdictions, newer derivatives such as AB‐FUBINACA ( 2 ) and MDMB‐CHMICA ( 3 ) appeared to replace them . SCRAs represent the largest and most chemically heterogeneous class of NPS, and new examples continue to emerge in drug markets around the world …”

Section: Introductionmentioning

confidence: 99%

“…5,6 SCRAs represent the largest and most chemically heterogeneous class of NPS, and new examples continue to emerge in drug markets around the world. [7][8][9][10][11][12] Unlike early SCRA NPS, many recent SCRAs have no precedent in the scientific literature when first detected in drug markets, necessitating robust analytical workflows for identification. 13 Even for the most well-studied SCRA NPS, existing data pertain to the activity of these compounds in cellular systems or animal models, [14][15][16][17][18][19][20][21] with very few human studies reported.…”

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confidence: 99%

“…39 The aim of the present work was to prepare and analytically characterize these emergent SCRAs and several analogs, and to evaluate their cannabinoid receptor affinities and activities in vitro and in vivo. Related analogs arising from expansion (7,8), or scission (9, 10) of the pyrrolidine ring were also prepared and evaluated to provide insight into structure-activity relationships (SARs) for this class.…”

mentioning

confidence: 99%

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The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

Banister

Kevin

Martin

et al. 2019

Drug Testing and Analysis

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5F‐PY‐PICA and 5F‐PY‐PINACA are pyrrolidinyl 1‐(5‐fluoropentyl)ind (az)ole‐3‐carboxamides identified in 2015 as putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS). 5F‐PY‐PICA, 5F‐PY‐PINACA, and analogs featuring variation of the 1‐alkyl substituent or contraction, expansion, or scission of the pyrrolidine ring were synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography–quadrupole time‐of‐flight–mass spectrometry (LC–QTOF–MS). In competitive binding experiments against HEK293 cells expressing human cannabinoid receptor type 1 (hCB1) or type 2 (hCB2), all analogs showed minimal affinity for CB1 (pKi < 5), although several demonstrated moderate CB2 binding (pKi 5.45–6.99). In fluorescence‐based membrane potential assays using AtT20‐hCB1 or ‐hCB2 cells, none of the compounds (at 10 μM) produced an effect >50% of the classical cannabinoid agonist CP55,940 (at 1 μM) at hCB1, although several showed slightly higher relative efficacy at hCB2. Expansion of the pyrrolidine ring of 5F‐PY‐PICA to an azepane (8) conferred the greatest hCB2 affinity (pKi 6.99) and activity (pEC50 7.54, Emax 72%) within the series. Unlike other SCRA NPS evaluated in vivo using radio biotelemetry, 5F‐PY‐PICA and 5F‐PY‐PINACA did not produce cannabimimetic effects (hypothermia, bradycardia) in mice at doses up to 10 mg/kg.

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Section: Nmr Spectroscopy Methodssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

Banister

Kevin

Martin

et al. 2019

Drug Testing and Analysis

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“…It is well known that SCs having a heat-unstable core skeleton of (1 H -indole)-3-carboxylate tend to give analytical artifacts, resulting from the transesterification reaction, when they are analyzed by GC–MS in the presence of methanol or ethanol [23, 24]. The degradation and esterification occur in the injection port of the GC instrument.…”

Section: Resultsmentioning

confidence: 99%

Analytical differentiation of quinolinyl- and isoquinolinyl-substituted 1-(5-fluoropentyl)-1H-indole-3-carboxylates: 5F-PB-22 and its ten isomers

Kohyama¹,

Chikumoto²,

Tada³

et al. 2016

Forensic Toxicol

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Differentiation among regioisomers of synthetic cannabinoids in forensic drug analysis is a crucial issue, since all isomers are not regulated by law. New equivalent analogs obtained via minor modification of their preexisting molecules keep on emerging. Isomers formed via substitutional exchange are also a cause for concern. This study is focused on the isomeric molecules that stem from minor modifications of 5F-PB-22. The analytical properties of these molecules and methods of differentiation are reported. Scan mode analysis using gas chromatography–electron ionization-mass spectrometry (GC–EI-MS) was performed using the authentic 5F-PB-22 standard, five regioisomeric quinolinyl ester indoles, and five regioisomeric isoquinolinyl ester indoles. Because it was not possible to separate 5F-PB-22 from the 5-hydroxyquinoline isomer using GC and all analytes showed similar EI mass spectra, liquid chromatography (LC)–tandem mass spectrometry analysis was performed. Using LC, a successful separation of 5F-PB-22 from all isomers could be achieved. Based on the electrospray ionization-mass spectra, the protonated molecular ion at m/z 377.2 was selected as the precursor ion for the regioisomeric and structural isomeric differentiation. Collision-induced dissociation provides relative intensity differences in the product ions among the isomers, enabling mass spectrometric differentiation of the isomers. To our knowledge, this is the first report on mass spectrometric differentiation of 5F-PB-22 and its ten isomers.Electronic supplementary materialThe online version of this article (doi:10.1007/s11419-016-0334-9) contains supplementary material, which is available to authorized users.

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Identification and analytical characterization of six synthetic cannabinoids NNL‐3, 5F–NPB‐22‐7N, 5F–AKB‐48‐7N, 5F–EDMB‐PINACA, EMB‐FUBINACA, and EG‐018

Liu

Wang

Hua

et al. 2017

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 phenomenon. The number of synthetic cannabinoids, the chemical diversity, and the speed of emergence make this group of compounds particularly challenging in terms of detection, monitoring, and responding. Three indazole 7N positional isomer synthetic cannabinoids, two ethyl 2-amino-3-methylbutanoate-type synthetic cannabinoids, and one 9H-carbazole substituted synthetic cannabinoid were identified in seized materials. These six synthetic cannabinoid derivatives included: 1H-benzo[d] [1,2,3]triazol-1-yl 1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (NNL-3, 1), quinolin-8-yl 1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (5F-NPB-22-7N, 2), N-((1 s,3 s)-adamantan-1-yl)-1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide (5F-AKB-48-7N, 3), ethyl 2-(1-(5-fluoropentyl)-1H-indazole-3-carboxamido)-3,3-dimethylbutanoate (5F-EDMB-PINACA, 4), ethyl 2-(1-(4-fluorobenzyl)-1H-indazole-3-carboxamido)-3-methylbutanoate (EMB-FUBINACA, 5), and naphthalen-1-yl(9-pentyl-9H-carbazol-3-yl)methanone (EG-018, 6). 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 spectroscopy (NMR). The analytical characterization of these six synthetic cannabinoids was described, so as 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 1-5 have appeared until now, making this the first report on these compounds. The GC-MS data of 6 has been reported, but this study added the LC-MS, NMR, and Fourier transform infrared (FTIR), data to render the analytical data collection process more complete. Copyright © 2017 John Wiley & Sons, Ltd.

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Identification of the novel synthetic cannabimimetic 8-quinolinyl 4-methyl-3-(1-piperidinylsulfonyl)benzoate (QMPSB) and other designer drugs in herbal incense

Cited by 19 publications

References 19 publications

The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

Analytical differentiation of quinolinyl- and isoquinolinyl-substituted 1-(5-fluoropentyl)-1H-indole-3-carboxylates: 5F-PB-22 and its ten isomers

Identification and analytical characterization of six synthetic cannabinoids NNL‐3, 5F–NPB‐22‐7N, 5F–AKB‐48‐7N, 5F–EDMB‐PINACA, EMB‐FUBINACA, and EG‐018

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