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

Author:

Chen Rui‐Jia12ORCID,Zhang Zi‐hua12,Yang Shenglan3,Yu Shu‐chen12,Wang Jun‐chang12,Liao Ping‐yong12,Qiu Ting‐ting12,Xiao Lu12,Xue Shang12,Chen Hong12,Shao Wen‐bin12,Hu Jian‐wen12,Lan Yun12,Chen Xi‐long12,Xu Yue12,Zhou Tian‐meng12,Zhao Xue‐jun12,Liu Wen‐bin12

Affiliation:

1. Shanghai Key Laboratory of Crime Scene Evidence Shanghai Research Institute of Criminal Science and Technology Shanghai China

2. Shanghai Yuansi Standard Science and Technology Co., Ltd Shanghai China

3. College of Materials Science and Engineering, National Engineering Research Center for Magnesium Alloys Chongqing University Chongqing China

Abstract

Abstract5F‐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.

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Publisher

Wiley

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