Distinguishing of 2‐MAPB and 6‐MAPB: Solution of the problem

Шевырин, Вадим А.; Shafran, Yuri

doi:10.1002/jms.3970

Cited by 6 publications

(3 citation statements)

References 13 publications

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“…However, the legislative measures for 2-MAPB are far less stringent than those for 5-MAPB, for example in some countries, 5-MAPB is regulated but there are no controls on 2-MAPB. 5 Most NPSs are isomers, and the lack of reference standards poses a great challenge for the structural identification of them in forensic laboratories. Nuclear magnetic resonance (NMR) spectroscopy is a valuable tool in the identification of isomers.…”

Section: Introductionmentioning

confidence: 99%

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Structural confirmation of position isomers 2‐(2‐methylaminoprolyl)benzofuran and 5‐(2‐methylaminopropyl)benzofuran: a combined mass spectrometric and computational study

Xu,

Lin,

Chen

et al. 2023

Rapid Comm Mass Spectrometry

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RationalePhenylethylamines are one of the most common types of new psychoactive substances, following synthetic cannabinoids and synthetic cathinones. They are regulated in many countries because of their strong hallucinogenic effects, which can cause serious nerve damage. There is a wide variety of phenylethylamines, exhibiting rapid renewal and extremely similar structures, therefore accurate qualitative analysis of isomers is a difficult problem in current drug analysis.MethodsThe dissociation pathways of the position isomers 2‐(2‐methylaminoprolyl)benzofuran (2‐MAPB) and 5‐(2‐methylaminopropyl)benzofuran (5‐MAPB) were investigated by gas chromatography–mass spectrometry and liquid chromatography coupled to high‐resolution quadrupole Orbitrap MS. The dissociation patterns of the phenethylamine‐based designer drugs 2‐MAPB and 5‐MAPB were explored and extended in this work based on MS combined with density functional theory studies.ResultsFor electron ionization mass spectrometry (EI‐MS) analysis, the dissociation patterns of 2‐MAPB were similar to those of 5‐MAPB. For electrospray ionization mass spectrometry (ESI‐MSn) analysis, the hydrogen atom on amino group was facile to form a intramolecular hydrogen bond with the oxygen atom on the parent nucleus of benzofuran in the structure of 2‐MAPB, leading to higher abundance of the product ion at m/z 58. However, there was a conjugated system between the positive charge formed by the cleavage of the 5‐MAPB side chain and the benzofuran ring, enabling the 5‐MAPB to generate a product ion at m/z 131. Computational study showed that energy barrier and spin density difference distribution jointly control the selective dissociation in EI‐MS, while different types of orbital interaction induced by intramolecular hydrogen bond led to different dissociation results in ESI‐MSn.ConclusionsThese different dissociation patterns could be used to distinguish 2‐MAPB from 5‐MAPB. This could assist forensic laboratories in the differentiation and characterization of potential isomers in these kinds of compounds, especially in mixtures.

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Section: Introductionmentioning

confidence: 99%

“…2‐(2‐methylaminoprolyl)benzofuran (2‐MAPB) is an isomer of 5‐MAPB that was detected in illegal transaction in 2015. However, the legislative measures for 2‐MAPB are far less stringent than those for 5‐MAPB, for example in some countries, 5‐MAPB is regulated but there are no controls on 2‐MAPB 5 …”

Section: Introductionmentioning

confidence: 99%

Structural confirmation of position isomers 2‐(2‐methylaminoprolyl)benzofuran and 5‐(2‐methylaminopropyl)benzofuran: a combined mass spectrometric and computational study

Xu,

Lin,

Chen

et al. 2023

Rapid Comm Mass Spectrometry

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“…[9][10][11] It not only provides full spectra with high sensitivity in first-stage mode (TOF spectra) but also acquires product ions spectrum with accurate masses in second-stage mode (Q-TOF spectra) to eliminate co-eluting signals and improve qualification accuracy. [12][13][14] In order to investigate whether the incense is ambergris or not, 7 modern ambergris were collected to build a reference database. The composition features of ambergris extract were studied via FT-IR and GC-QMS.…”

Section: Introductionmentioning

confidence: 99%

Characterization of the residues in glass bottle from the Song Dynasty by GC-QTOF---the earliest archaeological recorded ambergris at present

Ding

Fu³

et al. 2020

Preprint

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The organic residues in a glass bottle excavated from the Grand Baoen Temple site in the Song Dynasty, in Jiangsu Province, were studied in this paper. The Fourier transform infrared (FT-IR) spectroscopy, Gas chromatography–quadrupole mass spectrometry (GC-QMS) and Gas chromatography quadrupole time-of-flight mass spectrometry (GC-QTOF-MS) were applied to characterize the material. By comparing the 7 modern collected ambergris reference samples, the residue in the bottle was identified as ambergris. The biomarker molecule ambrein was detected in the residues via solvent vent mode and the co-eluent of interferent was checked using secondary Q-TOF mode. Furthermore, the occurrence of ambergris in the underground palace demonstrates the well-developed overseas incense trade and the solemn Buddhist culture of using incense in the Song Dynasty.

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Mass Spectrometry Applications in Forensic Science

Smith

Tran

2019

Encyclopedia of Analytical Chemistry

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Mass spectrometry (MS) is a technique widely used in forensic science for the identification of molecular or elemental composition of submitted evidence. Relatively small, volatile, nonpolar molecules, such as ignitable liquids and some drugs, can be analyzed with electron and chemical ionization (CI) coupled with single‐stage mass analyzers that provide molecular weight and structural information. Nonvolatile and polar molecules such as other drugs, poisons, and/or their metabolites can be identified using electrospray or related soft ionization techniques. The use of tandem MS with these compounds allows structure elucidation and provides excellent screening and quantitative results. Ambient ionization sources allow sampling directly from a surface with minimal sample preparation required. Elemental profiles also provide reliable methods for distinguishing between forensic samples. This article aims to provide an overview of the MS instrumentation, techniques, and applications within the field of forensic science.

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Distinguishing of 2‐MAPB and 6‐MAPB: Solution of the problem

Cited by 6 publications

References 13 publications

Structural confirmation of position isomers 2‐(2‐methylaminoprolyl)benzofuran and 5‐(2‐methylaminopropyl)benzofuran: a combined mass spectrometric and computational study

Structural confirmation of position isomers 2‐(2‐methylaminoprolyl)benzofuran and 5‐(2‐methylaminopropyl)benzofuran: a combined mass spectrometric and computational study

Characterization of the residues in glass bottle from the Song Dynasty by GC-QTOF---the earliest archaeological recorded ambergris at present

Mass Spectrometry Applications in Forensic Science

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