Metabolism of four novel structural analogs of ketamine, 2‐FXE [2‐(ethylamino)‐2‐(2‐fluorophenyl) cyclohexan‐1‐one], 2‐MDCK [2‐(methylamino)‐2‐(o‐tolyl) cyclohexan‐1‐one], 3‐DMXE [2‐(ethylamino)‐2‐(m‐tolyl) cyclohexan‐1‐one], and 2‐DMXE [2‐(ethylamino)‐2‐(o‐tolyl) cyclohexan‐1‐one], in human liver microsomes based on ultra‐performance liquid chromatography–high‐resolution tandem mass spectrometry

Author:

Hu Wen12ORCID,Liu Cuimei23,Hua Zhendong23,Li Jing23,Li Zhiyu12

Affiliation:

1. College of Pharmacy China Pharmaceutical University Nanjing China

2. Office of China National Narcotics Control Commission‐China Pharmaceutical University Joint Laboratory on Key Technologies of Narcotics Control Nanjing China

3. Key Laboratory of Drug Monitoring and Control Drug Intelligence and Forensic Center, Ministry of Public Security Beijing China

Abstract

AbstractNew psychoactive substances are constantly emerging, among which ketamine analogs with the core structure of 2‐amino‐2‐phenylcyclohexanone have attracted global attention due to their continued involvement in acute intoxications. The monitoring of these substances largely relies on the acquisition of metabolic data. However, the lack of in vitro human metabolism information for these emerging structural analogs presents significant challenges to drug control efforts. To address this challenge, we investigated the first‐phase metabolism patterns of four novel ketamine structural analogs of 2‐FXE [2‐(ethylamino)‐2‐(2‐fluorophenyl) cyclohexan‐1‐one], 2‐MDCK [2‐(methylamino)‐2‐(o‐tolyl) cyclohexan‐1‐one], 3‐DMXE [2‐(ethylamino)‐2‐(m‐tolyl) cyclohexan‐1‐one], and 2‐DMXE [2‐(ethylamino)‐2‐(o‐tolyl) cyclohexan‐1‐one] utilizing human liver microsomes for the first time. Metabolites were identified using ultra‐performance liquid chromatography coupled with high‐resolution tandem mass spectrometry. Our findings reveal that N‐dealkylation and hydroxylation are the primary metabolic reactions, alongside other notable reactions, including oxidation, reduction, and dehydration. Based on our extensive research, we propose N‐dealkylation and hydroxylation metabolites as appropriate analytical markers for monitoring the consumption of these substances.

Funder

National Key Research and Development Program of China

Publisher

Wiley

Subject

Clinical Biochemistry,Drug Discovery,Pharmacology,Molecular Biology,General Medicine,Biochemistry,Analytical Chemistry

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