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Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants

Brandt, SD, Carlino, L, Kavanagh, PV, Westphal, F, Dreiseitel, W, Dowling, G, Baumann, MH, Sitte, HH and Halberstadt, AL (2020) Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants. Drug Testing and Analysis, 12 (8). pp. 1109-1125. ISSN 1942-7603

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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 heptfluorobutyric anhydride and ethyl chloroformate (or heptfluorobutyric 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.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Brandt, SD, Carlino, L, Kavanagh, PV, et al. Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants. Drug Test Anal. 2020; 12: 1109– 1125, which has been published in final form at https://doi.org/10.1002/dta.2813. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Uncontrolled Keywords: 0301 Analytical Chemistry, 1115 Pharmacology and Pharmaceutical Sciences
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 30 Apr 2020 10:32
Last Modified: 12 Jan 2022 16:30
DOI or ID number: 10.1002/dta.2813
URI: https://researchonline.ljmu.ac.uk/id/eprint/12858
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