Abstract The substituted phenethylamine analogues in this study are derivatives of N-(2-methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine (25B-NBOMe) having the reverse substitution pattern for the two aromatic rings. These compounds contain only a single methoxy substituent in the phenethylamine part, and a bromodimethoxy substitution pattern in the benzyl portion. The regioisomers were prepared with variations in the substitution pattern in both the bromodimethoxy substitution pattern of the benzyl part as well as the methoxy substitution pattern in the phenethylamine part. The nine regioisomeric compounds were prepared from the regioisomeric 2-, 3-, and 4- methoxyphenethylamines via N-reductive alkylation with the three regioisomeric 2,4,5-substituted bromodimethoxybenzaldehydes. The EI-MS spectra of these regioisomers gave two major bromine containing ions at m/z 229/231 (base peak) and 258/260 and two non-brominated fragments at m/z 91 and 121. The relative abundance of the m/z 91 was higher for the 2-methoxyphenethylamine isomers and the relative abundance of the m/z 121 fragment was higher in the 4-methoxy isomer. The gas chromatographic separation for the regioisomeric methoxyphenethylamines of each bromodimethoxybenzyl aromatic ring substitution pattern showed the 2-methoxyphenethylamine substituted isomer eluted first followed by the 3-substituted isomer and the 4-methoxyphenethylamine substituted isomer was the last to elute and the three bromodimethoxybenzyl regioisomers for the 2-methoxyphenethylamine subseries were resolved as the trifluoroacetamides. The EI-MS for the TFA derivatives of the 2-bromo-4,5-dimethoxybenzyl isomers gave unique fragment ions resulting from displacement of bromine from the molecular ion. This fragmentation pathway was confirmed using the model compounds N-(2-, 3- and 4-bromobenzyl)phenethylamine trifluoroacetamides .

中文翻译：

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N-（溴二甲氧基苄基）-2-、3- 和 4-甲氧基苯乙胺的 GC-MS 分析：精神活性 25B-NBOMe 药物的反向类似物

摘要 本研究中取代的苯乙胺类似物是N-(2-甲氧基苄基)-4-溴-2,5-二甲氧基苯乙胺(25B-NBOMe)的两个芳环具有反向取代模式的衍生物。这些化合物在苯乙胺部分仅包含一个甲氧基取代基，在苄基部分包含溴二甲氧基取代模式。区域异构体是在苄基部分的溴二甲氧基取代模式和苯乙胺部分的甲氧基取代模式中以取代模式变化的方式制备的。九种区域异构化合物是由区域异构的 2-、3- 和 4- 甲氧基苯乙胺通过 N-还原性烷基化与三种区域异构的 2,4,5-取代的溴二甲氧基苯甲醛制备的。这些区域异构体的 EI-MS 谱图给出了 m/z 229/231（基峰）和 258/260 处的两个主要含溴离子以及 m/z 91 和 121 处的两个非溴化碎片。 2-甲氧基苯乙胺异构体的 z 91 更高，而 4-甲氧基异构体的 m/z 121 碎片的相对丰度更高。每个溴二甲氧基苄基芳环取代模式的区域异构甲氧基苯乙胺的气相色谱分离显示，首先洗脱的是 2-甲氧基苯乙胺取代的异构体，然后是 3-取代的异构体，最后洗脱的是 4-甲氧基苯乙胺取代的异构体，并且三个溴二甲氧基苯甲基的区域异构体被洗脱出来。 2-甲氧基苯乙胺亚系列被解析为三氟乙酰胺。2-溴-4 的 TFA 衍生物的 EI-MS，5-二甲氧基苄基异构体产生独特的碎片离子，这是由于溴从分子离子中置换出来的。使用模型化合物 N-(2-、3- 和 4-溴苄基) 苯乙胺三氟乙酰胺证实了该断裂途径。