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Identification of a new synthetic cannabinoid in a herbal mixture: 1-butyl-3-(2-methoxybenzoyl)indole

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Abstract

Two unknown cannabimimetic compounds were detected in a seized herbal mixture after gas chromatography–mass spectrometry (GC–MS) screening. To elucidate the chemical structures, 0.3 g of the dried plant material was extracted with methanol and concentrated under reduced pressure. The extract was purified by silica gel column chromatography with methylene chloride and methanol. Pure compounds were isolated by preparative high-performance liquid chromatography (HPLC) and then analyzed by electrospray ionization (ESI) mass spectrometry (MS) with direct flow injection, high-resolution ESI-time-of-flight (TOF)–MS and one-dimensional and two-dimensional nuclear magnetic resonance (NMR) spectroscopy. GC–MS spectra showed that the base ion at m/z 321 for compound 1 was the same as that of 1-pentyl-3-(4-methoxybenzoyl)indole (RCS-4), and the fragment ions were almost the same as those of RCS-4. The GC–MS spectrum of compound 2 was very similar to that of compound 1 except that the mass numbers of the fragment ions at m/z 290, 200, 186, and 173 of compound 2 were equally smaller than those of compound 1 by 14 amu. From these GC–MS results, compound 1 was assumed to be the 2- or 3-methoxy isomer of RCS-4, and compound 2 was assumed to be a 1-butylindole homologue of compound 1. The ESI mass spectra showed a single peak at m/z 322.33 for compound 1 and a single peak at m/z 308.25 for compound 2, which showed the masses of the protonated ions. High-resolution TOF–MS spectra showed the accurate mass numbers of protonated molecular ions at m/z 322.180512 for compound 1 and at m/z 308.164895 for compound 2, suggesting the molecular formulas of C21H23NO2 and C20H21NO2, respectively. The 1H NMR spectra showed signals that suggested 23 and 21 protons for compounds 1 and 2, respectively, while the respective 13C NMR spectra showed 21 and 20 carbon signals. All protons and carbons were assigned by their couplings and correlations observed in 1H–1H correlation spectroscopy (COSY), 1H–13C heteronuclear multiple bond correlation (HMBC), and 1H–13C heteronuclear single quantum coherence (HSQC) spectra. On the basis of the spectral data, compound 1 was identified as the 2-methoxy isomer of RCS-4; compound 2 was identified for the first time as 1-butyl-3-(2-methoxybenzoyl)indole. Phenazepam and 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT) were also identified as coexisting drugs in the herbal mixture. The contents of compounds 1 and 2 in the mixture were calculated to be 22.4 and 3.45 mg/g, respectively.

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Acknowledgments

The authors thank Prof. D.C. Moon of Chungbuk National University of South Korea for valuable discussion on the GC–MS results.

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Authors and Affiliations

  1. Forensic Chemistry Division, Southern District Office of National Forensic Service, Yangsan, 626-815, South Korea

    Yujin Park, Heesang Lee, Jaesung Pyo, Jiyeong Jo, Suncheun Kim & Sanggil Choe

  2. Narcotic Analysis Division, National Forensic Service, Seoul, South Korea

    Jaesin Lee & Hyeyoung Choi

  3. College of Pharmacy, Chungbuk National University, Cheongju, South Korea

    Chul Lee, Ran Seon Hong & Bang Yeon Hwang

  4. College of Pharmacy, Pusan National University, Busan, 609-735, South Korea

    Yonghoon Park & Jee H. Jung

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  1. Yujin Park
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  2. Chul Lee
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Correspondence to Sanggil Choe or Jee H. Jung.

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Park, Y., Lee, C., Lee, H. et al. Identification of a new synthetic cannabinoid in a herbal mixture: 1-butyl-3-(2-methoxybenzoyl)indole. Forensic Toxicol 31, 187–196 (2013). https://doi.org/10.1007/s11419-012-0173-2

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  • DOI: https://doi.org/10.1007/s11419-012-0173-2

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