Abstract：
N-Benzylphenethylamine derivatives are 5-HT2A receptor agonists with hallucinogenic properties, including NBOMe (N-(2-methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-amine) and NBOH (2-(((2,5-dimethoxyphenethyl)amino)methyl)phenol). We reported here the case of a 23-year-old man who presented a serotoninergic syndrome and a loss of consciousness following the consumption of a powder labelled as 25I-NBOH. Toxicological analyses of biological samples were carried out using a liquid chromatography high-resolution mass spectrometry. Two new psychoactive substances were identified and confirmed with certified reference materials: 25E-NBOH (2-(((4-ethyl-2,5-dimethoxyphenethyl)amino)methyl)phenol) and MDPHP (1-(benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one). Pharmaceuticals administered to the patient during his medical care were found in plasma and urine. 25E-NBOH and MDPHP concentrations were respectively at 2.3 ng/mL and 3.4 ng/mL in plasma, and 25.7 ng/mL and 30.5 ng/mL in urine. 25I-NBOH (2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol) was specifically searched in both samples and was not detected. These results are discussed along with a literature review on human cases of exposure to N-benzylphenethylamine derivatives. Using molecular networking approach, we propose the first 25E-NBOH metabolism study using authentic biological samples (plasma and urine). We described seven metabolites (M1 to M7), including two phase I (m/z 330.172; m/z 288.160) and five phase II metabolites (m/z 464.191, m/z 478.207, m/z 492.223, m/z 508.218; m/z 396.156). The M6 (m/z 492.223) was the most intense ion detected in plasma and urine and could be proposed as a relevant 25E-NBOH consumption marker. Overall, we described an original case of 25E-NBOH poisoning and identified metabolites that could potentially be used as consumption markers to detect 25E-NBOH intoxications with a higher confidence level and probably a longer detection window.
摘要：
N-苄基苯乙胺衍生物是具有致幻特性的5-HT2A受体激动剂，包括NBOMe(N-(2-甲氧基苄基)-2-(3,4,5-三甲氧基苯基)乙-1-胺)和NBOH(2-((2,5-二甲氧基苯乙基)氨基)甲基)苯酚。我们在此报告了一名23岁男子的病例，该男子在食用标记为25I-NBOH的粉末后出现5-羟色胺能综合征和意识丧失。使用液相色谱高分辨率质谱法对生物样品进行毒理学分析。通过认证的参考材料鉴定并确认了两种新的精神活性物质：25E-NBOH（2-（（（4-乙基-2,5-二甲氧基苯乙基）氨基）甲基）苯酚和MDPHP（1-（苯并[d][1,3]二氧杂环戊醇-5-基）-2-（吡咯烷-1-基）己-1-酮）。在患者的医疗护理期间给药的药物在血浆和尿液中被发现。25E-NBOH和MDPHP在血浆中的浓度分别为2.3ng/mL和3.4ng/mL，和25.7ng/mL和30.5ng/mL的尿液。25I-NBOH(2-(((4-碘-2,5-二甲氧基苯乙基)氨基)甲基)苯酚)在两个样品中均被特异性地搜索并且未被检测到。讨论了这些结果以及有关暴露于N-苄基苯乙胺衍生物的人类病例的文献综述。使用分子网络方法，我们提出了第一个使用真实生物样本（血浆和尿液）的25E-NBOH代谢研究。我们描述了七种代谢物（M1至M7），包括两个I相（m/z330.172；m/z288.160）和五个II相代谢物（m/z464.191，m/z478.207，m/z492.223，m/z508.218；m/z396.156）。M6(m/z492.223)是在血浆和尿液中检测到的最强离子,并且可以被提出作为相关的25E-NBOH消耗标记。总的来说,我们描述了一例25E-NBOH中毒的原始病例,并确定了可能用作消费标志物的代谢物,以更高的置信水平和可能更长的检测窗口检测25E-NBOH中毒.
