合成大麻素MDMB-CHMICA的化学特征分析：鉴定和评估缉获和合成样品中合成相关杂质的稳定性，并进行稳定性研究。,Drug Testing and Analysis

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合成大麻素MDMB-CHMICA的化学特征分析：鉴定和评估缉获和合成样品中合成相关杂质的稳定性，并进行稳定性研究。
Drug Testing and Analysis ( IF 2.6 ) Pub Date : 2019-06-17 , DOI: 10.1002/dta.2652
Sascha Münster-Müller _{1,

2} , Steven Hansen ₃ , Till Opatz ₃ , Ralf Zimmermann _{2,

4} , Michael Pütz ₁

Affiliation

在这项工作中，从癫痫发作和合成大麻素MDMB-CHMICA（甲基（S）-2-（1-（环己基甲基）-1 H表征了吲哚-3-羧酰胺基）3,3-二甲基丁酸酯。基于61种可用的MDMB-CHMICA粉末样品，评估了15种主要杂质，通过快速色谱法对其进行了大量分离，并通过高分辨率质谱和核磁共振波谱对结构进行了阐明和表征。除了验证杂质与主要成分的关系外，用独特的结构元素解释其化学结构还为制造过程和所使用的前体化合物提供了初步的见识。在对15个主要杂质进行液相色谱质谱分析后，评估了61个缉获的MDMB-CHMICA样品并根据相应的相对峰面积通过多元数据分析进行了分类。在这项工作的第二部分，进行了MDMB-CHMICA稳定性测试和多重受控合成，以更好地了解杂质特征的变化并评估被检样品中杂质模式变化的重要性。氨基酸与1-（环己基甲基）-1的最后偶联步骤H-吲哚-3-羧酸是使用偶联剂草酰氯，亚硫酰氯和HATU进行的。此外，研究了反应时间和温度对杂质分布的影响。总体而言，在受控测试中发现了八种新杂质，在稳定性测试过程中发现了两种MDMB-CHIMCA降解产物。在同一天进行的合成重复实验显示出相似的杂质特征。在不同的日子，他们表现出可辨别的签名。使用不同的偶联剂或条件可以清楚地区分杂质。

"点击查看英文标题和摘要"

Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples.

In this work, the most discriminating synthesis‐related impurities found in samples from seizures and controlled synthesis of the synthetic cannabinoid MDMB‐CHMICA (methyl (S)‐2‐(1‐(cyclohexylmethyl)‐1H‐indole‐3‐carboxamido)‐3,3‐dimethylbutanoate) were characterized. Based on 61 available powder samples of MDMB‐CHMICA, 15 key‐impurities were assessed, isolated in larger quantities via flash chromatography and structurally elucidated and characterized via high resolution mass spectrometry and nuclear magnetic resonance spectroscopy. Apart from verifying the relation of the impurities to the major component, the interpretation of their chemical structures with distinct structural elements provided first insights into the manufacturing process and the precursor compounds used. Following liquid chromatography mass spectrometry analysis of the 15 key‐impurities, the 61 seized samples of MDMB‐CHMICA were evaluated and classified via multivariate data analysis based on the corresponding relative peak areas. In a second part of this work, stability tests and multiple controlled syntheses of MDMB‐CHMICA were carried out to better understand variations in impurity signatures and to assess the significance of variations in the impurity patterns of seized samples. The last coupling step of the amino acid with 1‐(cyclohexylmethyl)‐1H‐indole‐3‐carboxylic acid was performed using the coupling agents oxalyl chloride, thionyl chloride, and HATU. Furthermore, the impact of reaction time and temperature on the impurity profile were investigated. Overall, eight new impurities were found in the controlled syntheses and two degradation products of MDMB‐CHIMCA were found in the course of the stability tests. Replicates of a synthesis conducted on the same day showed similar impurity signatures; on different days they showed discriminable signatures. The use of different coupling reagents or conditions gave clearly distinguishable impurity signatures.

更新日期：2019-06-17

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