Structure elucidation of the novel synthetic cannabinoid Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) found in illicit products in Germany
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Benedikt Pulver
- Torsten Schoenberger
- Diana Weigel
- Matthias Koeck
- Yvonne Eschenlohr
- Tobias Lucas
- Nika Podlesnik
- Till Opatz
- Wolfgang Dreiseitel
- Michael Puetz
- Jan Schaeper
- Andrea Jacobsen-Bauer
- Volker Auwaerter
- Folker Westphal
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000779573300001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1002/dta.3261
- eISSN
- 1942-7611
- Externe Identifier
- Clarivate Analytics Document Solution ID: 3N0SE
- PubMed Identifier: 35338591
- ISSN
- 1942-7603
- Ausgabe der Veröffentlichung
- 8
- Zeitschrift
- DRUG TESTING AND ANALYSIS
- Schlüsselwörter
- GC artefact
- NPS
- pharmacology
- structure elucidation
- synthetic cannabinoid
- Paginierung
- 1387 - 1406
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Titel
- Structure elucidation of the novel synthetic cannabinoid Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) found in illicit products in Germany
- Sub types
- Article
- Ausgabe der Zeitschrift
- 14
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>New chemical moieties continue to appear in synthetic cannabimimetics (SC), the largest group of new psychoactive substances in the EU. We describe the first comprehensive characterisation of the novel SC Cumyl‐To<jats:styled-content>s</jats:styled-content>yl‐<jats:styled-content>I</jats:styled-content><jats:styled-content>n</jats:styled-content>dazole‐3‐<jats:styled-content>Ca</jats:styled-content>rbox<jats:styled-content>a</jats:styled-content>mide (Cumyl‐TsINACA) (<jats:italic>N</jats:italic>‐[2‐phenylpropan‐2‐yl]‐1‐tosyl‐1<jats:italic>H</jats:italic>‐indazole‐3‐carboxamide) from seized case samples. Structure elucidation was performed within the EU‐project ADEBAR <jats:italic>plus</jats:italic> to facilitate confident identification by other researchers and practitioners worldwide. Characteristic MS fragmentations include the cleavage of the sulfonamide bond (S‐N), the aryl sulfone bond (C‐S) and the elimination rearrangement of SO<jats:sub>2</jats:sub> in the side chain. Cumyl‐TsINACA is a full receptor agonist at <jats:italic>h</jats:italic>CB<jats:sub>1</jats:sub> (E<jats:sub>max</jats:sub> = 228%) with very weak binding affinity (<jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> = 292 n<jats:sc>m</jats:sc>) and low functional activity (EC<jats:sub>50</jats:sub> = 31 μ<jats:sc>m</jats:sc>). Thermal degradation of Cumyl‐TsINACA was observed under GC conditions. The degree to which the tosyl side chain is cleaved due to pyrolysis primarily depends on solvent, the use of glass wool in the liner and injector temperature. The determination of the constitution by NMR spectroscopy was ambiguous due to the high number of neighbouring, non‐proton‐bearing atoms. Therefore, other possible structures compatible with the NMR correlations were generated using the WebCocon software. The unambiguous structural evidence was finally obtained by spectra comparison after the synthesis of Cumyl‐TsINACA. The low thermal stability, as well as the low affinity and potency, renders this compound unfavourable for the use as a psychoactive substance. Thus, we do not expect widespread adoption of this SC.</jats:p>
- Autoren
- Benedikt Pulver
- Torsten Schönberger
- Diana Weigel
- Matthias Köck
- Yvonne Eschenlohr
- Tobias Lucas
- Nika Podlesnik
- Till Opatz
- Wolfgang Dreiseitel
- Michael Pütz
- Jan Schäper
- Andrea Jacobsen‐Bauer
- Volker Auwärter
- Folker Westphal
- DOI
- 10.1002/dta.3261
- eISSN
- 1942-7611
- ISSN
- 1942-7603
- Ausgabe der Veröffentlichung
- 8
- Zeitschrift
- Drug Testing and Analysis
- Sprache
- en
- Online publication date
- 2022
- Paginierung
- 1387 - 1406
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/dta.3261
- Datum der Datenerfassung
- 2023
- Titel
- Structure elucidation of the novel synthetic cannabinoid Cumyl‐Tosyl‐Indazole‐3‐Carboxamide (Cumyl‐TsINACA) found in illicit products in Germany
- Ausgabe der Zeitschrift
- 14
Datenquelle: Crossref
- Abstract
- New chemical moieties continue to appear in synthetic cannabimimetics (SC), the largest group of new psychoactive substances in the EU. We describe the first comprehensive characterisation of the novel SC Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) (N-[2-phenylpropan-2-yl]-1-tosyl-1H-indazole-3-carboxamide) from seized case samples. Structure elucidation was performed within the EU-project ADEBAR plus to facilitate confident identification by other researchers and practitioners worldwide. Characteristic MS fragmentations include the cleavage of the sulfonamide bond (S-N), the aryl sulfone bond (C-S) and the elimination rearrangement of SO<sub>2</sub> in the side chain. Cumyl-TsINACA is a full receptor agonist at hCB<sub>1</sub> (E<sub>max</sub> = 228%) with very weak binding affinity (K<sub>i</sub> = 292 nm) and low functional activity (EC<sub>50</sub> = 31 μm). Thermal degradation of Cumyl-TsINACA was observed under GC conditions. The degree to which the tosyl side chain is cleaved due to pyrolysis primarily depends on solvent, the use of glass wool in the liner and injector temperature. The determination of the constitution by NMR spectroscopy was ambiguous due to the high number of neighbouring, non-proton-bearing atoms. Therefore, other possible structures compatible with the NMR correlations were generated using the WebCocon software. The unambiguous structural evidence was finally obtained by spectra comparison after the synthesis of Cumyl-TsINACA. The low thermal stability, as well as the low affinity and potency, renders this compound unfavourable for the use as a psychoactive substance. Thus, we do not expect widespread adoption of this SC.
- Addresses
- Institute of Forensic Medicine, Forensic Toxicology, Medical Center, Faculty of Medicine, University of Freiburg, Freiburg, Germany.
- Autoren
- Benedikt Pulver
- Torsten Schönberger
- Diana Weigel
- Matthias Köck
- Yvonne Eschenlohr
- Tobias Lucas
- Nika Podlesnik
- Till Opatz
- Wolfgang Dreiseitel
- Michael Pütz
- Jan Schäper
- Andrea Jacobsen-Bauer
- Volker Auwärter
- Folker Westphal
- DOI
- 10.1002/dta.3261
- eISSN
- 1942-7611
- Externe Identifier
- PubMed Identifier: 35338591
- Funding acknowledgements
- Internal Security Fund of the European Union: IZ25-5793-2019-33
- Open access
- false
- ISSN
- 1942-7603
- Ausgabe der Veröffentlichung
- 8
- Zeitschrift
- Drug testing and analysis
- Schlüsselwörter
- Cannabinoids
- Indazoles
- Magnetic Resonance Spectroscopy
- Germany
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2022
- Paginierung
- 1387 - 1406
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum der Datenerfassung
- 2022
- Titel
- Structure elucidation of the novel synthetic cannabinoid Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) found in illicit products in Germany.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 14
Datenquelle: Europe PubMed Central
- Abstract
- New chemical moieties continue to appear in synthetic cannabimimetics (SC), the largest group of new psychoactive substances in the EU. We describe the first comprehensive characterisation of the novel SC Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) (N-[2-phenylpropan-2-yl]-1-tosyl-1H-indazole-3-carboxamide) from seized case samples. Structure elucidation was performed within the EU-project ADEBAR plus to facilitate confident identification by other researchers and practitioners worldwide. Characteristic MS fragmentations include the cleavage of the sulfonamide bond (S-N), the aryl sulfone bond (C-S) and the elimination rearrangement of SO2 in the side chain. Cumyl-TsINACA is a full receptor agonist at hCB1 (Emax = 228%) with very weak binding affinity (Ki = 292 nm) and low functional activity (EC50 = 31 μm). Thermal degradation of Cumyl-TsINACA was observed under GC conditions. The degree to which the tosyl side chain is cleaved due to pyrolysis primarily depends on solvent, the use of glass wool in the liner and injector temperature. The determination of the constitution by NMR spectroscopy was ambiguous due to the high number of neighbouring, non-proton-bearing atoms. Therefore, other possible structures compatible with the NMR correlations were generated using the WebCocon software. The unambiguous structural evidence was finally obtained by spectra comparison after the synthesis of Cumyl-TsINACA. The low thermal stability, as well as the low affinity and potency, renders this compound unfavourable for the use as a psychoactive substance. Thus, we do not expect widespread adoption of this SC.
- Date of acceptance
- 2022
- Autoren
- Benedikt Pulver
- Torsten Schönberger
- Diana Weigel
- Matthias Köck
- Yvonne Eschenlohr
- Tobias Lucas
- Nika Podlesnik
- Till Opatz
- Wolfgang Dreiseitel
- Michael Pütz
- Jan Schäper
- Andrea Jacobsen-Bauer
- Volker Auwärter
- Folker Westphal
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/35338591
- DOI
- 10.1002/dta.3261
- eISSN
- 1942-7611
- Funding acknowledgements
- Internal Security Fund of the European Union: IZ25-5793-2019-33
- Ausgabe der Veröffentlichung
- 8
- Zeitschrift
- Drug Test Anal
- Schlüsselwörter
- GC artefact
- NPS
- pharmacology
- structure elucidation
- synthetic cannabinoid
- Cannabinoids
- Germany
- Indazoles
- Magnetic Resonance Spectroscopy
- Sprache
- eng
- Country
- England
- Paginierung
- 1387 - 1406
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2022
- Titel
- Structure elucidation of the novel synthetic cannabinoid Cumyl-Tosyl-Indazole-3-Carboxamide (Cumyl-TsINACA) found in illicit products in Germany.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 14
Datenquelle: PubMed
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