Differentiation of o-, m-, and p-fluoro-α-pyrrolidinopropiophenones by Triton B-mediated one-pot reaction
| Autor: | Naoki Asao, Satoshi Chinaka, Rahul D. Kavthe, Takaya Murakami, Hiroshi Hasegawa, Reiko Ishimaru, Yoshiaki Iwamuro |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Benzyltrimethylammonium hydroxide
010401 analytical chemistry chemistry.chemical_element Mass spectrometry 01 natural sciences Medicinal chemistry 0104 chemical sciences Pathology and Forensic Medicine Adduct Catalysis 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine chemistry Mass spectrum Fluorine Structural isomer 030216 legal & forensic medicine Methanol Law |
| Zdroj: | Forensic science international. 302 |
| ISSN: | 1872-6283 |
| Popis: | Positional isomer differentiation is crucial for the analysis of forensic drugs. Presently, it is difficult to distinguish among ortho, meta, and para positional isomers of ring-fluorinated synthetic cathinones, a major class of new psychoactive substances (NPSs), because they exhibit similar chromatographic properties and mass spectral patterns. We describe herein that the ring-fluorinated synthetic cathinone positional isomers, viz. o-, m-, and p-fluoro-α-pyrrolidinopropiophenones (o-, m-, and p-FPPPs), can be discriminated by their benzyltrimethylammonium hydroxide (Triton B)-mediated one-pot reaction with methanol at ambient temperature, followed by chromatographic and mass spectral analyses of the corresponding products. For p-FPPP, fluorine was nucleophilically substituted by the methoxy group to afford p-methoxy-α-pyrrolidinopropiophenone, while o- and m-FPPPs afforded the corresponding FPPP-enamine-pyrrolidine adducts, which allowed the above positional isomers to be unambiguously differentiated by comparing the reaction product chromatograms and mass spectra. The adopted approach, which does not require excess heating or use of metallic catalysts and features the advantages of simplicity and convenience, is expected to contribute toward practical NPS identification. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect