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Forensic Science International
Two thiazolylindoles and a benzimidazole: Novel compounds on the designer drug market with potential cannabinoid receptor activity Folker Westphal, Frank D. Sönnichsen, Siegfried Knecht, Volker Auwärter, Laura Huppertz Forensic Science International Volume 249, Pages (April 2015) DOI: /j.forsciint Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 1 EI-MS spectrum (top) and CI-MS spectrum of 1 (bottom).
Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 2 EI-MS spectrum (top) and CI-MS spectrum of 2 (bottom).
Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 3 Acquired and simulated LC-HRMS-spectrum of compound 1 with suggested molecular formulae (SmartFormula). Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 4 Extracted chromatogram traces of C23H34N3OS and C23H34N3O3, illustrating the presence of one sulfur atom instead of two oxygens. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 5 Acquired and simulated LC-HRMS-spectrum of compound 2 with suggested molecular formulae (SmartFormula). Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 6 Extracted chromatogram traces of C21H30N3S and C21H30N3O2, illustrating the presence of one sulfur atom instead of two oxygens. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 7 bbCID spectrum and extracted chromatographic traces of compound 1 and its fragments with suggested molecular formulae (SmartFormula). Signals not deriving from the precursor are not annotated (non-parallel EICs). EICs of and are not illustrated due to their relatively low intensity. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 8 bbCID spectrum and extracted chromatographic traces of compound 2 and its fragments with suggested molecular formulae (SmartFormula). Signals not deriving from the precursor are not annotated (non-parallel EICs). Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 9 IR spectrum of 1 (top) and detail (bottom).
Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 10 IR spectrum of 2 (top) and detail (bottom).
Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 11 NMR assignments of N-(2-methoxyethyl),N-iso-propyl-2-(1-pentyl-1H-indol-3-yl)-4-thiazolemethanamine(1). s: singlet; d: doublet t: triplet; q: quartet; p: pentet; sept: septet; m: multiplet. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 12 NMR assignments of N,N-diethyl-2-(1-pentyl-1H-indol-3-yl)-4-thiazolemethanamine(2), abbreviations for multiplicities of 1H signals see Fig. 11. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 13 Possible fragmentation pathways for m/z 213, 227 and 283 after CI/ESI. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 14 3-([1,3]-thiazol-2-yl)indoles with CB1 receptor activity according to [16–18]. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 15 EI-MS spectrum (top) and CI-MS spectrum of 6 (bottom).
Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 16 Acquired and simulated spectrum of compound 6 after LC-HRMS with suggested molecular formulae (SmartFormula). Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 17 bbCID spectrum and extracted chromatographic traces of compound 6 and its fragments with suggested molecular formulae (SmartFormula). Signals not deriving from the precursor are not annotated (non-parallel EICs). Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 18 IR spectrum of 6 (top) and detail (bottom).
Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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Fig. 19 NMR assignments of 1-(cyclohexylmethyl)-2-[(4-ethoxyphenyl)methyl]-N,N-diethyl-1H-benzimidazol-5-carboxamide(6), AB: AB-system; br: broad; other abbreviations for multiplicities of 1H signals see Fig. 11. Forensic Science International , DOI: ( /j.forsciint ) Copyright © 2015 Elsevier Ireland Ltd Terms and Conditions
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