Abstract
PurposeA 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.MethodsThese 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.ResultsThe 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.ConclusionsThe 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.
Highlights
A psychotropic synthetic cannabinoid (SC) BB-22 [quinolin-8-yl 1-(cyclohexylmethyl)-1H-indole-3-carboxylate], shown in Fig. 1, was firstly identified in herbal-type illegal products in 2013 [1]
Serum and urine specimens from healthy subjects, under their permission with informed consent, were used as blank samples, and those spiked with several amounts of BB-22 and BB-22 3-carboxyindole were used as quality control samples
The selected reaction monitoring (SRM) chromatograms by liquid chromatography (LC)–MS/MS are shown for the detection of BB-22 (Fig. 2a), where the extract from blank urine spiked with the reference standard at 1.0 ng/mL, the extract from serum in case 2, the extract from β-glucuronide-hydrolyzed urine in case 2, the extract from blank urine and the extract from blank urine spiked with internal standard (IS) at 1.0 ng/mL are shown from the top to the bottom
Summary
A psychotropic synthetic cannabinoid (SC) BB-22 [quinolin-8-yl 1-(cyclohexylmethyl)-1H-indole-3-carboxylate], shown in Fig. 1, was firstly identified in herbal-type illegal products in 2013 [1]. A psychotropic synthetic cannabinoid (SC) BB-22 [quinolin-8-yl 1-(cyclohexylmethyl)-1H-indole-3-carboxylate], shown, was firstly identified in herbal-type illegal products in 2013 [1]. The first generation SC, JWH-018, was active toward the C B1 receptor having an affinity 4.5 times higher than that of ∆9-tetrahydrocannabinol contained naturally in Cannabis sativa, while the affinity of BB-22 was reported to be about 30 times higher than that of JWH-018 [2]. As to the concentrations of BB-22 in any authentic human specimens, one study reported on its plasma level, 97 pg/mL, based on liquid chromatography.
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