Synthesis, structural characterization, analytical profiling, and application to authentic samples of synthesized Phase I metabolites of the synthetic cannabinoid 5F‐MDMB‐PICA,Drug Testing and Analysis

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Synthesis, structural characterization, analytical profiling, and application to authentic samples of synthesized Phase I metabolites of the synthetic cannabinoid 5F‐MDMB‐PICA
Drug Testing and Analysis ( IF 2.6 ) Pub Date : 2024-03-16 , DOI: 10.1002/dta.3680
Rui-Jia Chen _{1,

2} , Zi-Hua Zhang _{1,

2} , Shenglan Yang ₃ , Shu-Chen Yu _{1,

2} , Jun-Chang Wang _{1,

2} , Ping-Yong Liao _{1,

2} , Ting-Ting Qiu _{1,

2} , Lu Xiao _{1,

2} , Shang Xue _{1,

2} , Hong Chen _{1,

2} , Wen-Bin Shao _{1,

2} , Jian-Wen Hu _{1,

2} , Yun Lan _{1,

2} , Xi-Long Chen _{1,

2} , Yue Xu _{1,

2} , Tian-Meng Zhou _{1,

2} , Xue-Jun Zhao _{1,

2} , Wen-Bin Liu _{1,

2}

Affiliation

5F‐MDMB‐PICA, an indole‐type synthetic cannabinoid (SC), was classified illicit globally in 2020. Although the extensive metabolism of 5F‐MDMB‐PICA in the human body warrants the development of robust analytical methods for metabolite detection and quantification, a current lack of reference standards for characteristic metabolites hinders such method creation. This work described the synthesis of 18 reference standards for 5F‐MDMB‐PICA and its possible Phase I metabolites, including three hydroxylated positional isomers R14 to R16. All the compounds were systematic characterized via nuclear magnetic resonance, Fourier transform infrared spectroscopy, and high‐resolution mass spectrometry. Furthermore, two methods were developed for the simultaneous detection of all standards using liquid chromatography–tandem mass spectrometry and ultra‐performance liquid chromatography–quadrupole time‐of‐flight mass spectrometry. By comparison with authentic samples, R17 was identified as a suitable urine biomarker for 5F‐MDMB‐PICA uptake.

中文翻译：

合成大麻素 5F-MDMB-PICA 的合成 I 期代谢物的合成、结构表征、分析谱和真实样品的应用

5F-MDMB-PICA 是一种吲哚型合成大麻素 (SC)，于 2020 年在全球被列为非法。尽管 5F-MDMB-PICA 在人体内的广泛代谢需要开发强大的代谢物检测和定量分析方法，目前缺乏特征代谢物的参考标准阻碍了这种方法的创建。这项工作描述了 5F-MDMB-PICA 及其可能的 I 期代谢物的 18 种参考标准品的合成，包括三种羟基化位置异构体 R14 至 R16。所有化合物均通过核磁共振、傅里叶变换红外光谱和高分辨率质谱进行系统表征。此外，还开发了两种使用液相色谱-串联质谱和超高效液相色谱-四极杆飞行时间质谱同时检测所有标准品的方法。通过与真实样品进行比较，R17 被确定为 5F-MDMB-PICA 摄取的合适尿液生物标志物。

更新日期：2024-03-16

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