合成mdmb (n) -073f大麻模拟物及其在生物材料中的标记物的分析特性

S. S. Kataev, O. Dvorskaya, M. Gofenberg, A. Labutin, A. Melentyev
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To carry out the study, the following materials were used: plant-based objects with narcotic drugs withdrawn from illegal trafficking and applied to them;. urine samples to be studied under chemical-toxicological and forensic and chemical analyses. For solid-phase epitaxy, SampliQ EVIDEX TFE cartridges – 200 mg – 3 ml (Agilent, USA) were used for sample preparation; β-glucuronidase, Type HP-2, From Helix Pomatia, 100000 UA/ml (Sigma-ALDRICH CHEMI, Germany) was used for enzymatic hydrolysis. GC-MS/MS analysis was made using Agilent 7890 gas chromatograph with a tandem quadrupolar mass-spectrometer Agilent 7000 (Agilent, США); GC-MS analysis was carrid out using gas chromatograph Agilent 7820 with mass-selective detector Agilent 5975 (Agilent, USA); HPLC-HRMS research was made on liquid chromatograph Agilent 1260 with tandem hybrid high-resolution quadrupole-time-of-flight detector Agilent 6540 (Agilent, США); liquid chromatograph Agilent 1260 with Agilent 6460 (Agilent, USA) with tandem mass-spectrometer were used for making HPLC-MS/MS research.Results. The structure of MDMB(N)-073F compound has been confirmed and an exact mass of the protonated molecule corresponding to the chemical formula C19H27FN3O3 fixed by GC-MS/MS and HPLC-HRMS methods. Spectral characteristics of MDMB(N)-073F have been given. One of the branches in MDMB(N)-073F biotransformation in the human body found out by GC-MS and HPLC-MS/MS methods, is the ester decomposition with further conjugation of the resulting acid. The product interacting with glucuronic acid, is found to be the conjugate of major MDMB(N)-073F metabolite of the Ist phase in biotransformation. Metabolites appearing due to the ester decomposition and its conjugate with glucuronic acid, are recommended to be used as markers for synthetic MDMB(N)-073F cannabimimetics in the analysis by chromatographic methods; they can be used for regular screening of biological samples.Conclusion. 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引用次数: 1

摘要

本研究旨在利用气相色谱-串联质谱(GC-MS)和高效液相色谱-高分辨率质谱(HPLC-HRMS)相结合的方法,研究合成的MDMB(N)-073F大麻仿物吲哚唑羧基的分析特征,以及MDMB(N)-073F主要代谢物、葡萄糖醛酸盐及其衍生物的特征。采用气相色谱-质谱(GC-MS)检测和高效液相色谱(HPLC) -质谱联用(HPLC-MS/MS)对尿样进行分析,应用于专家实践、化学毒理学、法医和化学分析。材料和方法。为了进行这项研究,使用了以下材料:从非法贩运中撤出的麻醉药品的植物性物体并应用于它们;尿液样本将在化学毒理学、法医和化学分析下进行研究。固相外延:样品制备采用SampliQ EVIDEX TFE - 200 mg - 3 ml(美国安捷伦公司);β-葡萄糖醛酸酶,HP-2型,来自Helix Pomatia, 100000 UA/ml (Sigma-ALDRICH CHEMI,德国)用于酶解。采用Agilent 7890气相色谱仪和Agilent 7000串联四极质谱仪(Agilent, США)进行GC-MS/MS分析;采用气相色谱仪Agilent 7820和质量选择检测器Agilent 5975 (Agilent, USA)进行GC-MS分析;在Agilent 1260液相色谱仪和串联混合高分辨率四极杆飞行时间检测器Agilent 6540 (Agilent, США)上进行HPLC-HRMS研究;采用Agilent 1260液相色谱仪和Agilent 6460(美国Agilent公司)串联质谱仪进行HPLC-MS/MS研究。通过GC-MS/MS和HPLC-HRMS方法确定了MDMB(N)-073F化合物的结构,并确定了分子式C19H27FN3O3对应的质子化分子的确切质量。给出了MDMB(N)-073F的光谱特性。通过GC-MS和HPLC-MS/MS方法发现MDMB(N)-073F在人体内生物转化的一个分支是酯分解并进一步偶联生成酸。该产物与葡萄糖醛酸相互作用,是生物转化过程中主要MDMB(N)-073F代谢物的偶联物。由于酯分解产生的代谢产物及其与葡萄糖醛酸的结合,推荐作为合成MDMB(N)-073F大麻模拟物的色谱分析标记物;可用于生物样品的常规筛选。本文提出的研究结果如下:通过气相色谱-串联质谱(GC-MS/ MS)和液相色谱混合高分辨率四极杆飞行时间质谱(HPLC-HRMS)相结合的方法,发现合成MDMB(N)-073F大麻模拟物的分析特征,以及MDMB(N)-073F主要代谢物的特征;利用气相色谱-质谱联用检测(GC-MS)和液相色谱-串联质谱联用(HPLC-MS/MS)在尿样中的葡萄糖醛酸盐及其衍生物应用于专家实践、化学毒理学、法医和化学分析。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
ANALYTICAL FEATURES OF SYNTHETIC MDMB(N)-073F CANNABIMIMETICS AND ITS MARKERS IN BIOLOGICAL MATERIAL
The aim of the research is to study both analytical features of synthetic MDMB(N)-073F cannabimimetics of indazole carboxamides group by gas chromatography methods combined with tandem mass spectrometry (GC-MS) and high performance liquid chromatography with high-resolution mass spectrometry (HPLC-HRMS) as well as characteristics of the major MDMB(N)-073F metabolite, its glucuronide and derivatives, using gas chromatography with mass-spectrometric (GC-MS) detection and high-performance liquid chromatography (HPLC) with MS/MS mass spectrometry (HPLC-MS/MS) in urine samples to be applied in expert practice, chemical-toxicological and forensic and chemical analyses.Materials and methods. To carry out the study, the following materials were used: plant-based objects with narcotic drugs withdrawn from illegal trafficking and applied to them;. urine samples to be studied under chemical-toxicological and forensic and chemical analyses. For solid-phase epitaxy, SampliQ EVIDEX TFE cartridges – 200 mg – 3 ml (Agilent, USA) were used for sample preparation; β-glucuronidase, Type HP-2, From Helix Pomatia, 100000 UA/ml (Sigma-ALDRICH CHEMI, Germany) was used for enzymatic hydrolysis. GC-MS/MS analysis was made using Agilent 7890 gas chromatograph with a tandem quadrupolar mass-spectrometer Agilent 7000 (Agilent, США); GC-MS analysis was carrid out using gas chromatograph Agilent 7820 with mass-selective detector Agilent 5975 (Agilent, USA); HPLC-HRMS research was made on liquid chromatograph Agilent 1260 with tandem hybrid high-resolution quadrupole-time-of-flight detector Agilent 6540 (Agilent, США); liquid chromatograph Agilent 1260 with Agilent 6460 (Agilent, USA) with tandem mass-spectrometer were used for making HPLC-MS/MS research.Results. The structure of MDMB(N)-073F compound has been confirmed and an exact mass of the protonated molecule corresponding to the chemical formula C19H27FN3O3 fixed by GC-MS/MS and HPLC-HRMS methods. Spectral characteristics of MDMB(N)-073F have been given. One of the branches in MDMB(N)-073F biotransformation in the human body found out by GC-MS and HPLC-MS/MS methods, is the ester decomposition with further conjugation of the resulting acid. The product interacting with glucuronic acid, is found to be the conjugate of major MDMB(N)-073F metabolite of the Ist phase in biotransformation. Metabolites appearing due to the ester decomposition and its conjugate with glucuronic acid, are recommended to be used as markers for synthetic MDMB(N)-073F cannabimimetics in the analysis by chromatographic methods; they can be used for regular screening of biological samples.Conclusion. The research results presented here, are the following: the analytical features characteristic for synthetic MDMB(N)-073F cannabimimetics found out by gas chromatography methods combined with tandem mass spectrometry (GC-MS/ MS) and liquid chromatography of hybrid high-resolution quadrupole-time-of-flight mass spectrometry (HPLC-HRMS), as well as characteristics of major MDMB(N)-073F metabolite, its glucuronide and derivatives with the use of gas chromatography with mass-spectrometric detection (GC-MS) and liquid chromatography combined with tandem mass spectrometry (HPLC-MS/MS) in urine samples to be applied in expert practice, chemical-toxicological, forensic and chemical analyses.
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