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Street-Like Synthesis of Krokodil Results in the Formation of an Enlarged Cluster of Known and New Morphinans
Chemical Research in Toxicology ( IF 3.7 ) Pub Date : 2017-08-04 00:00:00 , DOI: 10.1021/acs.chemrestox.7b00126
José Xavier Soares 1 , Emanuele Amorim Alves 2, 3, 4, 5 , André M. N. Silva 6 , Natália Guimarães de Figueiredo 7 , João F. Neves 8 , Sara Manuela Cravo 8 , Maria Rangel 9 , Annibal Duarte Pereira Netto 10 , Félix Carvalho 2 , Ricardo Jorge Dinis-Oliveira 2, 3, 5 , Carlos Manuel Afonso 8, 11
Affiliation  

“Krokodil” is the street name for a homemade injectable drug that has been used as a cheap substitute for heroin. Codeine is the opioid starting material for krokodil synthesis, and desomorphine is claimed to be the main opioid of krokodil and the main component responsible for its addictive and psychoactive characteristics. However, due to its peculiar manufacture, using cheap raw materials, krokodil is composed of a large and complex mixture of different substances. In order to shed some light upon the chemical complexity of krokodil, its profiling was conducted by reverse phase high performance liquid chromatography coupled to a photodiode array detector (RP-HPLC-DAD) and by liquid chromatography coupled to high resolution tandem mass spectrometry (LC-ESI-IT-Orbitrap-MS). Besides desomorphine, codeine, and morphine, profiting from the high resolution mass spectrometry (HRMS) data, an endeavor to study the morphinans content in krokodil was set for the first time. Considering codeine as the only morphinan precursor and the possible chemical transformations that can occur during krokodil synthesis, the morphinan chemical space was designed, and 95 compounds were defined. By making use of the morphinan chemical space in krokodil, the exact masses featured by HRMS, and the morphinan mass fragmentations patterns, a targeted identification approach was designed and implemented.The proposed 95 morphinans were searched using the full scan chromatogram of krokodil, and findings were validated by mass fragmentation of the correspondent precursor ions (MS2 spectra). Following this effort, a total of 54 morphinans were detected, highlighting the fact that these additional morphinans may contribute to the psychotropic effects of krokodil.

中文翻译:

Krokodil的类似于街道的合成导致形成已知的和新的吗啡酮扩大簇

“ Krokodil”是一种自制可注射药物的街道名称,该药物已被用作海洛因的廉价替代品。可待因是克罗可地合成的阿片样物质起始原料,而去甲吗啡据称是克罗可地的主要阿片样物质,并且是其成瘾性和精神活性特征的主要成分。但是,由于其廉价的原料制造而成的奇异果糖醇,是由大量不同物质组成的复杂混合物。为了对克罗地尔的化学复杂性有一些了解,其分析是通过反相高效液相色谱联用光电二极管阵列检测器(RP-HPLC-DAD)以及液相色谱联用高分辨率串联质谱法(LC)进行的。 -ESI-IT-Orbitrap-MS)。除了去甲吗啡,可待因和吗啡外,得益于高分辨率质谱(HRMS)数据,我们首次尝试研究克罗可地中吗啡喃的含量。考虑可待因是唯一的吗啡喃前体,以及在克罗可地合成过程中可能发生的化学转化,设计了吗啡喃化学空间,并定义了95种化合物。通过利用克罗克地尔中的吗啡化学空间,HRMS的精确质量以及吗啡酸质量碎片模式,设计并实施了针对性的鉴定方法。利用克罗克地尔的全扫描色谱图搜索了拟议的95个吗啡喃,并发现了结果通过相应的前体离子(MS 首次研究了克罗克地尔中吗啡类成分的含量。考虑可待因是唯一的吗啡喃前体,以及在克罗可地合成过程中可能发生的化学转化,设计了吗啡喃化学空间,并定义了95种化合物。通过利用克罗克地尔中的吗啡化学空间,HRMS的精确质量以及吗啡酸质量碎片模式,设计并实施了针对性的鉴定方法。利用克罗克地尔的全扫描色谱图搜索了拟议的95个吗啡喃,并发现了结果通过相应的前体离子(MS 首次研究了克罗克地尔中吗啡类成分的含量。考虑可待因是唯一的吗啡喃前体,以及在克罗可地合成过程中可能发生的化学转化,设计了吗啡喃化学空间,并定义了95种化合物。通过利用克罗克地尔中的吗啡化学空间,HRMS的精确质量以及吗啡酸质量碎片模式,设计并实施了针对性的鉴定方法。利用克罗克地尔的全扫描色谱图搜索了拟议的95个吗啡喃,并发现了结果通过相应的前体离子(MS 定义了95种化合物。通过利用克罗克地尔中的吗啡化学空间,HRMS的精确质量以及吗啡酸质量碎片模式,设计并实施了针对性的鉴定方法。利用克罗克地尔的全扫描色谱图搜索了拟议的95个吗啡喃,并发现了结果通过相应的前体离子(MS 定义了95种化合物。通过利用克罗克地尔中的吗啡化学空间,HRMS的精确质量以及吗啡酸质量碎片模式,设计并实施了针对性的鉴定方法。利用克罗克地尔的全扫描色谱图搜索了拟议的95个吗啡喃,并发现了结果通过相应的前体离子(MS2个光谱)。经过这一努力,总共检测到54种吗啡,突显出这些额外的吗啡可能会促进克罗克地尔的精神作用。
更新日期:2017-08-04
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