Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA

Bovens, Michael; Bissig, Christian; Staeheli, Sandra N.; Poetzsch, Michael; Pfeiffer, Bernhard; Kræmer, Thomas

doi:10.1016/j.forsciint.2017.10.020

Cited by 33 publications

(32 citation statements)

References 9 publications

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“…The only peak that is common to all three compounds is m/z 119.08. The proposed fragmentation pathways shown in Figure are entirely consistent with those described extensively for 6 , 7 , and related analogs previously …”

Section: Resultssupporting

confidence: 84%

“…Assignment of signals was assisted by COSY, DEPT, HSQC, and HMBC experiments where necessary. Fourier‐transform infrared (FTIR) spectroscopy data were previously reported for these compounds, with no remarkable spectral differences noted …”

Section: Methodsmentioning

confidence: 85%

“…Similarly, the base peak for each compound corresponded to the acylium ion formed following loss of the cumylamine group and was observed at m/z 232.06 for 5 , and at one greater amu for 6 ( m/z 233.06) and 7 ( m/z 233.06). Other identifiable peaks include the likely products of a McLafferty rearrangement and subsequent elimination of methylstyrene of 5 , 6 , and 7 at m/z 248.11, 249.09, and 249.08, respectively, as described for related systems . The prominent ion m/z 352.15 observed for 6 corresponds to loss of a single methyl group from the cumylamine side chain, likely due to stabilization of the formed tertiary carbocation, but it is unclear why the corresponding ion was not observed for 5 or 7 .…”

Section: Resultsmentioning

confidence: 96%

“…SCRAs featuring pyrrolo[2,3‐ b ] pyridine cores and other bicyclic heteroaromatic scaffolds continue to be reported, and little is known about their pharmacology and toxicology . We prepared 5 , 6 , and 7 , and investigated methods for discrimination of these analogs using nuclear magnetic resonance (NMR) spectroscopy, gas chromatograph–mass spectrometry (GC–MS), and liquid chromatography–quadrupole time‐of‐flight–MS (LC–QTOF–MS).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

Banister

Adams

Kevin

et al. 2018

Drug Testing and Analysis

104

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Synthetic cannabinoid receptor agonists (SCRAs) are a dynamic class of new psychoactive substances (NPS), with novel chemotypes emerging each year. Following the putative detection of 5F-CUMYL-P7AICA in Australia in 2016, the scaffold-hopping SCRAs 5F-CUMYL-PICA, 5F-CUMYL-PINACA, and 5F-CUMYL-P7AICA were synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). Since little is known of the pharmacology of 7-azaindole SCRAs like 5F-CUMYL-P7AICA, the binding affinities and functional activities of all compounds at cannabinoid type 1 and type 2 receptors (CB and CB , respectively) were assessed using tritiated radioligand competition experiments and fluorescence-based plate reader membrane potential assays. Despite CB binding affinities differing by over two orders of magnitude (K = 2.95-174 nM), all compounds were potent and efficacious CB agonists (EC = 0.43-4.7 nM), with consistent rank order for binding and functional activity (5F-CUMYL-PINACA >5F-CUMYL-PICA >5F-CUMYL-P7AICA). Additionally, 5F-CUMYL-P7AICA was found to exert potent cannabimimetic effects in mice, inducing hypothermia (6°C, 3 mg/kg) through a CB -dependent mechanism.

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Section: Resultssupporting

confidence: 84%

Section: Methodsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

Banister

Adams

Kevin

et al. 2018

Drug Testing and Analysis

104

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“…Characterization of synthetic cannabinoids by electron impact mass spectrometry has been well documented . Nuclear magnetic resonance (NMR) spectroscopy is used for structural confirmation of unknown substances , but this technique is rarely available to state and local crime laboratories and is more frequently utilized by larger regional or federally funded agencies, as well as within academic institutions.…”

mentioning

confidence: 99%

4F‐MDMB‐BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework

Krotulski

Mohr

Kacinko³

et al. 2019

Journal of Forensic Sciences

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This is the first report regarding the characterization of the new synthetic cannabinoid 4F‐MDMB‐BINACA. 4F‐MDMB‐BINACA was first analytically confirmed in seized drug material using gas chromatography–mass spectrometry (GC‐MS), liquid chromatography–quadrupole time‐of‐flight mass spectrometry (LC‐QTOF), and nuclear magnetic resonance (NMR) spectroscopy. Subsequent to this characterization, 4F‐MDMB‐BINACA was detected in biological specimens collected as part of forensically relevant casework, including medicolegal death investigations and drug impaired driving investigations, from a variety of regions in the United States. Further analysis of biological specimens resulted in the identification of the metabolites 4F‐MDMB‐BINACA 3,3‐dimethylbutanoic acid and 4‐OH‐MDMB‐BINACA. 4F‐MDMB‐BINACA is appearing with increasing frequency as a contributory factor in deaths, creating morbidity and mortality risks for drug users. Laboratories must be aware of its presence and impact, incorporating 4F‐MDMB‐BINACA into workflows for detection and confirmation.

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¹H−¹⁵N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA

Martek

Mihelač

Gazvoda

et al. 2019

Drug Testing and Analysis

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The high frequency of the synthetic cannabinoid receptor agonists (SCRAs) emergence renders this group of new psychoactive compounds particularly demanding in terms of detection, identification, and responding. Without the available reference material, one of the specific problems is differentiation and structure elucidation of constitutional isomers. Herein, we report a simple and efficient flow chart diagram applicable for a rapid nuclear magnetic resonance (NMR) identification and differentiation between azaindoles, 4‐, 5‐, 6‐, and 7‐azaindole, which is a common structural motif of synthetic cannabinoids. The flow chart diagram is based on 1H NMR and 1H–15N NMR spectra, and to prove the concept, it has been tested on 5F‐MDMB‐P7AICA (1). Spectral and analytical data including standard 1D and 2D NMR spectra, gas chromatography−mass spectrometry (GC−MS), Fourier transform infrared−attenuated total reflectant (FTIR−ATR), Raman, melting point, and combustion analysis are provided for compound 1.

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Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA

Cited by 33 publications

References 9 publications

Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

4F‐MDMB‐BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework

¹H−¹⁵N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA

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Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA

Cited by 33 publications

References 9 publications

Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

Synthesis and pharmacology of new psychoactive substance 5F‐CUMYL‐P7AICA, a scaffold‐ hopping analog of synthetic cannabinoid receptor agonists 5F‐CUMYL‐PICA and 5F‐CUMYL‐PINACA

4F‐MDMB‐BINACA: A New Synthetic Cannabinoid Widely Implicated in Forensic Casework

1H−15N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA

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¹H−¹⁵N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA