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2019年至2023年期间在科威特查获的合成大麻素样品的鉴定及化学结构解析:采用气相色谱-质谱联用仪(GC-MS)和核磁共振光谱(NMR)技术

Identification and chemical structure elucidation of synthetic cannabinoids samples seized in Kuwait during 2019-2023 using GC-MS and NMR spectroscopy.

作者信息

Al-Matrouk Abdullah, Orabi Khaled Y

机构信息

Narcotic and Psychotropic Laboratory, Department of Criminal Evidence, Ministry of Interior, Kuwait City, Kuwait.

Department of Pharmaceutical Chemistry, College of Pharmacy, Health Sciences Center, Kuwait University, Safat, Kuwait.

出版信息

Forensic Sci Res. 2025 Apr 23;10(2):owae026. doi: 10.1093/fsr/owae026. eCollection 2025 Jun.

Abstract

Cannabinoids, a class of chemical compounds, interact with cannabinoid receptors and are categorized into endocannabinoids, phytocannabinoids, and synthetic cannabinoids (SCs) based on their origin. Among these, SCs constitute the largest and most structurally diverse group of novel psychoactive substances (NPS), with around 280 compounds identified globally. They exhibit a high binding affinity to cannabinoid receptors CB1 and CB2, which are distributed throughout the central nervous and immune systems, leading to more potent psychoactive and toxic effects compared with their natural counterparts. Various adverse effects associated with SCs include hypothermia, analgesia, catalepsy, psychosis, respiratory depression, cardiac arrest, nephrotoxicity, acute cerebral ischemia, seizures, and mortality. In a previous study, we reported the detection of several NPS in Kuwait using gas chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry techniques. However, the identification was tentative, highlighting a limitation of these methods. To address this, the current study aimed to fully identify 17 seized SC samples. Thin-layer chromatography was initially employed to assess the purity of the samples. Twelve pure samples (AKM-1-AKM-12) underwent nuclear magnetic resonance analyses, including H, C, DEPT 45°, 90°, 135°, COSY, HSQC, and HMBC experiments. The identities of five samples (AKM-1, 5, 6, 8, 10) were confirmed as MDMB-4en-PINACA, one sample (AKM-2) as 4F-MDMB-BUTICA, one sample (AKM-3) as MPHP-2201, and three samples (AKM-4, 9, 11) as MMB-022. Additionally, two samples (AKM-7, 12) were identified as FUB-144. This comprehensive approach enhances the accuracy of SCs identification compared with previous studies, emphasizing the importance of employing nuclear magnetic resonance alongside other spectral methods for a more robust analysis.

摘要

大麻素是一类化合物,与大麻素受体相互作用,并根据其来源分为内源性大麻素、植物性大麻素和合成大麻素(SCs)。其中,合成大麻素是新型精神活性物质(NPS)中数量最多、结构最多样化的一类,全球已鉴定出约280种化合物。它们对分布于中枢神经系统和免疫系统的大麻素受体CB1和CB2具有很高的结合亲和力,与天然大麻素相比,具有更强的精神活性和毒性作用。与合成大麻素相关的各种不良反应包括体温过低、镇痛、僵住症、精神病、呼吸抑制、心脏骤停、肾毒性、急性脑缺血、癫痫发作和死亡。在之前的一项研究中,我们报告了使用气相色谱-质谱联用和液相色谱-串联质谱技术在科威特检测到几种新型精神活性物质。然而,鉴定是初步的,突出了这些方法的局限性。为了解决这个问题,本研究旨在全面鉴定17个查获的合成大麻素样本。最初采用薄层色谱法评估样本的纯度。12个纯样本(AKM-1-AKM-12)进行了核磁共振分析,包括氢、碳、DEPT 45°、90°、135°、COSY、HSQC和HMBC实验。5个样本(AKM-1、5、6、8、10)被确认为MDMB-4en-PINACA,1个样本(AKM-2)为4F-MDMB-BUTICA,1个样本(AKM-3)为MPHP-2201,3个样本(AKM-4、9、11)为MMB-022。此外,2个样本(AKM-7、12)被鉴定为FUB-144。与之前的研究相比,这种综合方法提高了合成大麻素鉴定的准确性,强调了将核磁共振与其他光谱方法结合使用以进行更可靠分析的重要性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1dae/12038813/2d7a63ec5a84/owae026f1.jpg

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