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Sensitive quantification of 5F-PB-22 and its three metabolites 5F-PB-22 3-carboxyindole, B-22 N-5-hydroxypentyl and PB-22 N-pentanoic acid in authentic urine specimens obtained from four individuals by liquid chromatography–tandem mass spectrometry

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Abstract

Purpose

Urine is the most suitable specimen to collect from individuals because of noninvasiveness and relatively large volumes obtainable. In authentic urine specimens, however, synthetic cannabinoids having the structures of quinolinyl ester indoles, such as 5F-PB-22, PB-22 and BB-22, in unchanged forms as well as their metabolites, have not been quantified yet. Therefore, the aim of this study was to establish a sensitive analytical method for the quantification of 5F-PB-22 and its three metabolites 5F-PB-22 3-carboxyindole, PB-22 N-5-hydroxypentyl and PB-22 N-pentanoic acid in authentic urine samples in four cases.

Methods

These compounds were extracted from β-glucuronide-hydrolyzed and unhydrolyzed urine via liquid-liquid extraction. The identification and quantification were performed using the QTRAP type of a liquid chromatography–tandem mass spectrometer.

Results

The limits of detection were 3–30 pg/mL and their summed quantitation range was 10–10,000 pg/mL. The devised method was applied to quantify these compounds in authentic urine specimens obtained from four individuals. The levels of 5F-PB-22 were 5.1, 13.6, 94.7 and 470 pg/mL; those of 5F-PB-22 3-carboxyindole were 8.25, 3.39, 23.2 and 880 ng/mL; and those of PB-22 N-pentanoic acid were 12.0, 57.4, 959 and 2090 pg/mL, respectively, in four unhydrolyzed urine samples, and the levels of PB-22 N-5-hydroxypentyl could be quantified as 29.9 and 131 pg/mL in two unhydrolyzed urine samples.

Conclusions

The 5F-PB-22 and its metabolites PB-22 N-5-hydroxypentyl have been detected from authentic human urine samples for the first time. Also, this is the first report dealing with the quantification of the three metabolites in human urine samples.

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Acknowledgements

This work was supported by JSPS KAKENHI Grant number JP16K09206.

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Authors and Affiliations

  1. Department of Legal Medicine, Hamamatsu University School of Medicine, 1-20-1 Handayama, Higashi-ku, Hamamatsu, 431-3192, Japan

    Kayoko Minakata, Koutaro Hasegawa, Itaru Yamagishi, Hideki Nozawa, Osamu Suzuki & Kanako Watanabe

  2. National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan

    Ruri Kikura-Hanajiri

  3. Research Equipment Center, Hamamatsu University School of Medicine, 1-20-1 Handayama, Higashi-ku, Hamamatsu, 431-3192, Japan

    Masako Suzuki & Takuya Kitamoto

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  1. Kayoko Minakata
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Correspondence to Kayoko Minakata.

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The authors declare that there are no financial or other relationships that could lead to a conflict of interest.

Ethical approval

All procedures performed in this study involving human participants were in accordance with the ethical standards of the international and/or national committee and with the 1964 Declaration of Helsinki and its later amendments or comparable ethical standards. Informed consent was obtained from all participants included in the study, who supplied about 40 mL each of urine for use as blank samples. The analysis of toxic substances from the authentic human urine samples was permitted by judicial authorities and supported by official documentation.

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Minakata, K., Hasegawa, K., Yamagishi, I. et al. Sensitive quantification of 5F-PB-22 and its three metabolites 5F-PB-22 3-carboxyindole, B-22 N-5-hydroxypentyl and PB-22 N-pentanoic acid in authentic urine specimens obtained from four individuals by liquid chromatography–tandem mass spectrometry. Forensic Toxicol 36, 151–159 (2018). https://doi.org/10.1007/s11419-017-0395-4

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  • DOI: https://doi.org/10.1007/s11419-017-0395-4

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