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Forensic Toxicology
Published in: Forensic Toxicology 1/2019

Open Access 01-01-2019 | Original Article

Sensitive quantification of BB-22 and its metabolite BB-22 3-carboxyindole, and characterization of new metabolites in authentic urine and/or serum specimens obtained from three individuals by LC–QTRAP-MS/MS and high-resolution LC–Orbitrap-MS/MS

Authors: Kayoko Minakata, Koutaro Hasegawa, Hideki Nozawa, Itaru Yamagishi, Takeji Saitoh, Atsuto Yoshino, Masako Suzuki, Takuya Kitamoto, Osamu Suzuki, Kanako Watanabe

Published in: Forensic Toxicology | Issue 1/2019

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Abstract

Purpose

A synthetic cannabinoid BB-22 and its metabolite BB-22 3-carboxyindole have not yet been quantified in human urine. The aim of this study is to establish a sensitive analytical method for the quantification of BB-22 and its 3-carboxyindole in human serum and urine specimens, and the characterization of the unreported metabolites of BB-22 in authentic urine specimens from three individuals.

Methods

These compounds were extracted from β-glucuronide-hydrolyzed and unhydrolyzed urine and/or serum via liquid–liquid extraction. The identification and quantification were performed using liquid chromatography (LC)–QTRAP-tandem mass spectrometry (MS/MS) and the characterization of the new metabolites was made by high-resolution LC–MS/MS.

Results

The limits of detection of BB-22 and BB-22 3-carboxyindole were 3 and 30 pg/mL in urine, respectively. The devised method was applied to quantify these compounds in authentic serum and urine obtained from two drug abusers and in urine from one drug abuser. The serum levels of BB-22 were 149 and 6680 pg/mL, and those of BB-22 3-carboxyindole were 0.755 and 38.0 ng/mL in cases 1 and 2, respectively. The urine levels of BB-22 were 5.64, 5.52 and 6.92 pg/mL and those of BB-22 3-carboxyindole were 0.131, 21.4 and 5.15 ng/mL in cases 1, 2 and 3, respectively. New monohydroxyl metabolites retaining the structure of BB-22 were found in the urine specimens.

Conclusions

The synthetic cannabinoid BB-22 and its metabolite BB-22 3-carboxyindole were identified and quantified in authentic human serum and urine specimens for the first time, and new metabolites of BB-22 were tentatively identified in authentic urine specimens obtained from three drug users in this study.
Literature
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Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicol 31:223–240CrossRef
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Carlier J, Diao X, Huestis MA (2018) Synthetic cannabinoid BB-22 (QUCHIC): human hepatocytes metabolism with liquid chromatography-high resolution mass spectrometry detection. J Pharm Biomed Anal 157:27–35CrossRefPubMed
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Minakata K, Yamagishi I, Nozawa H, Hasegawa K, Suzuki M, Gonmori K, Suzuki O, Watanabe K (2017) Sensitive identification and quantitation of parent forms of six synthetic cannabinoids in urine samples of human cadavers by liquid chromatography–tandem mass spectrometry. Forensic Toxicol 35:275–283CrossRef
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Minakata K, Hasegawa K, Yamagishi I, Nozawa H, Kikura-Hanajiri R, Suzuki M, Kitamoto T, Suzuki O, Watanabe K (2018) Sensitive 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 specimens obtained from four individuals by liquid chromatography–tandem mass spectrometry. Forensic Toxicol 36:151–159CrossRef
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Minakata K, Nozawa H, Yamagishi I, Hasegawa K, Saitoh T, Yoshino A, Suzuki M, Kitamoto T, Suzuki O, Watanabe K (2018) Sensitive quantification of 5F-NNEI and characterization of its several metabolites in authentic urine and/or serum specimens obtained from three individuals by LC–QTRAP-MS/MS and high-resolution LC–Orbitrap-MS/MS. Forensic Toxicol 36:498–505CrossRef
Metadata
Title
Sensitive quantification of BB-22 and its metabolite BB-22 3-carboxyindole, and characterization of new metabolites in authentic urine and/or serum specimens obtained from three individuals by LC–QTRAP-MS/MS and high-resolution LC–Orbitrap-MS/MS
Authors
Kayoko Minakata
Koutaro Hasegawa
Hideki Nozawa
Itaru Yamagishi
Takeji Saitoh
Atsuto Yoshino
Masako Suzuki
Takuya Kitamoto
Osamu Suzuki
Kanako Watanabe
Publication date
01-01-2019
Publisher
Springer Singapore
Published in
Forensic Toxicology / Issue 1/2019
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-018-0448-3

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