Two groups of amphetamine‐like drugs with psychostimulant properties that were first developed during the course of scientific studies and later emerged as new psychoactive substances (NPS) are based on the (2‐aminopropyl)indole (API) and (2‐aminopropyl)benzofuran (APB) structural scaffolds. However, sulfur‐based analogs with a benzo[b]thiophene structure (resulting in (2‐aminopropyl)benzo[b]thiophene (APBT) derivatives) have received little attention. In the present investigation, all six racemic APBT positional isomers were synthesized in an effort to understand their structure–activity relationships relative to API‐ and APB‐based drugs. One lesson learned from the NPS phenomenon is that one cannot exclude the appearance of such substances on the market. Therefore, an in‐depth analytical characterization was performed, including various single‐ and tandem mass spectrometry (MS) and ionization platforms coupled to gas chromatography (GC) and liquid chromatography (LC), nuclear magnetic resonance spectroscopy (NMR), and solid phase and GC condensed phase infrared spectroscopy (GC‐sIR). Various derivatizations have also been explored; it was found that all six APBT isomers could be differentiated during GC analysis after derivatization with heptafluorobutyric anhydride and ethyl chloroformate (or heptafluorobutyric anhydride and acetic anhydride) under non‐routine conditions. Discriminating analytical features can also be derived from NMR, GC‐EI/CI‐ single‐ and tandem mass spectrometry, LC (pentafluorophenyl stationary phase), and various infrared spectroscopy approaches (including GC‐sIR). Availability of detailed analytical data obtained from these novel APBT‐type stimulants may be useful to researchers and scientists in cases where forensic and clinical investigations are warranted.

中文翻译：

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新型 (2-氨基丙基) 苯并 [b] 噻吩 (APBT) 基兴奋剂的合成和分析表征。

两组具有精神兴奋剂特性的苯丙胺类药物最初是在科学研究过程中开发出来的，后来成为新的精神活性物质 (NPS)，它们基于 (2-氨基丙基)吲哚 (API) 和 (2-氨基丙基)苯并呋喃(APB) 结构支架。然而，具有苯并[ b ]噻吩结构的硫基类似物（产生 (2-氨基丙基)苯并[ b]噻吩（APBT）衍生物）很少受到关注。在本研究中，合成了所有六种外消旋 APBT 位置异构体，以了解它们相对于 API 和 APB 药物的构效关系。从 NPS 现象中吸取的一个教训是，不能排除此类物质在市场上的出现。因此，进行了深入的分析表征，包括各种单质谱和串联质谱 (MS) 以及与气相色谱 (GC) 和液相色谱 (LC)、核磁共振光谱 (NMR) 和固相耦合的电离平台和 GC 凝聚相红外光谱 (GC-sIR)。还探索了各种衍生化；发现在非常规条件下用七氟丁酸酐和氯甲酸乙酯（或七氟丁酸酐和乙酸酐）衍生后，所有六种 APBT 异构体都可以在 GC 分析中得到区分。鉴别分析特征也可以从 NMR、GC-EI/CI-单质谱和串联质谱、LC（五氟苯基固定相）和各种红外光谱方法（包括 GC-sIR）中获得。在需要进行法医和临床调查的情况下，从这些新型 APBT 型兴奋剂获得的详细分析数据的可用性可能对研究人员和科学家有用。鉴别分析特征也可以从 NMR、GC-EI/CI-单质谱和串联质谱、LC（五氟苯基固定相）和各种红外光谱方法（包括 GC-sIR）中获得。在需要进行法医和临床调查的情况下，从这些新型 APBT 型兴奋剂获得的详细分析数据的可用性可能对研究人员和科学家有用。鉴别分析特征也可以从 NMR、GC-EI/CI-单质谱和串联质谱、LC（五氟苯基固定相）和各种红外光谱方法（包括 GC-sIR）中获得。在需要进行法医和临床调查的情况下，从这些新型 APBT 型兴奋剂获得的详细分析数据的可用性可能对研究人员和科学家有用。