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

Rui-Jia Chen; Zi-Hua Zhang; Shenglan Yang; Shu-Chen Yu; Jun-Chang Wang; Ping-Yong Liao; Ting-Ting Qiu; Lu Xiao; Shang Xue; Hong Chen; Wen-Bin Shao; Jian-Wen Hu; Yun Lan; Xi-Long Chen; Yue Xu; Tian-Meng Zhou; Xue-Jun Zhao; Wen-Bin Liu

doi:10.1002/dta.3680

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

Drug Test Anal. 2024 Mar 15. doi: 10.1002/dta.3680. Online ahead of print.

Authors

Rui-Jia Chen^{1

2}, Zi-Hua Zhang^{1

2}, Shenglan Yang³, 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}

Affiliations

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.

PMID: 38488339
DOI: 10.1002/dta.3680

Abstract

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.

Keywords: 5F-MDMB-PICA; metabolite standard; synthesized metabolite; synthetic cannabinoids.

Abstract

Grants and funding