Differentiation of FUB-JWH-018 positional isomers by electrospray ionization–triple quadrupole mass spectrometry

Chikumoto, Takao; Kadomura, Natsuki; Matsuhisa, Takaya; Kawashima, Hidenobu; Kohyama, Erina; Nagai, Hirokazu; Soda, Midori; Kitaichi, Kiyoyuki; Ito, Tetsuro

doi:10.1016/j.forc.2019.100157

Cited by 6 publications

(4 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…dithiocarboxylates, halogenated phenylmethylidene hydrazinecarbodithioates, and fluoromethcathinones, along with theoretical calculations for the interpretation of the resulting mass spectral data, has been performed. [26][27][28][29][30][31][32]…”

Section: S-methylmethoxylphenylmethylenehydrazinementioning

confidence: 99%

“…Energy‐minimized structures of the product ions and their energies were calculated, and heats of reaction for the formation of the product ions were used to explain the analysis results. Mass spectral differentiation of positional isomers such as dinitrotoluenes, aminodinitrotoluenes, S ‐methylmethoxylphenylmethylenehydrazine dithiocarboxylates, halogenated phenylmethylidene hydrazinecarbodithioates, and fluoromethcathinones, along with theoretical calculations for the interpretation of the resulting mass spectral data, has been performed 26–32 . Schwarzenberg et al differentiated 2‐amino‐4,6‐dinitrotoluene and 4‐amino‐2,6‐dinitrotoluene by analyzing them using electrospray ionization Fourier transform mass spectrometry and density functional theory (DFT) calculations 26 …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Characteristics of ionization behaviors of aminonitrotoluene isomers produced by atmospheric pressure chemical ionization

Choi

2022

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale: Six of the isomers of aminonitrotoluene (ANT) are 2-amino-3-nitrotoluene (2A3NT), 2A4NT, 2A5NT, 2A6NT, 4A2NT, and 4A3NT. Some of them can be identified by chromatography and spectroscopy. Biochemical transformation of 2,4,6-trinitrotoluene (TNT) and dinitrotoluenes (DNTs) is very complex and ANTs are decomposition products of TNT and DNTs.Methods: Each isomer in acetone was ionized using atmospheric pressure chemical ionization in positive and negative ion modes, and kinds and abundances of the product ions were analyzed. Energy-minimized structures of the product ions and their energies were calculated to explain the analysis results.

show abstract

Section: S-methylmethoxylphenylmethylenehydrazinementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Characteristics of ionization behaviors of aminonitrotoluene isomers produced by atmospheric pressure chemical ionization

Choi

2022

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…According to Murakami et al 9,11 and Chikumoto et al 12,21 , the fluoro positional isomers of SCs can be differentiated by the relative abundance of the two product ions in the collision-induced dissociation reaction using LC-MS. Based on these studies, we examined whether the iodo positional isomers of SCs can be differentiated in serum according to the difference in the relative abundances of product ions. To find the optimum CE for distinguishing positional meta and para isomers of C5-I by the product ion spectrum, the CE was changed from 10 to 60 eV in increments of 10 eV (Fig.…”

Section: Differentiation By Ms/msmentioning

confidence: 99%

Differentiation of Positional Isomers of Halogenated Benzoylindole Synthetic Cannabinoid Derivatives in Serum by Hybrid Quadrupole/Orbitrap Mass Spectrometry

et al. 2020

View full text Add to dashboard Cite

Legally regulated synthetic cannabinoids (SCs) are continuously being created by making minor positional modifications to pre-existing analogs; thus, compounds with minor structural differences must be isolated and identified accurately.For iodo-benzoylindole derivatives of SCs, only specific isomers are currently the target of legal control, and it is necessary to establish an analytical method for accurately identifying positional isomers.In this study, we synthesized a series of 57 designer drugs and developed a screening method for identifying halogen positional isomers on the phenyl ring of benzoylindole derivative SCs in serum. Analytical methods using the Discovery F5 pentafluorophenyl column gave the best selectivity and retention of the positional isomer analytes. Some of the meta and para iodo-substituted SCs were eluted at similar retention times and were difficult to separate by liquid chromatography (LC). However, they were identified via the relative abundance of the two product ions in the collision-induced dissociation reaction using LC-hybrid quadrupole/Orbitrap high-resolution mass spectrometry. Our synthesized halogen-substituted positional isomer SC library and method for differentiating positional isomers of halogenated benzoylindole SC derivatives could provide an indispensable analysis tool for identifying illegal drugs in serum of drug users.

show abstract

“…The most popular method for achieving this is gas chromatography combined with mass spectrometry (GC–MS). The sample can be separated by liquid chromatography (LC) and measured by electrospray ionization-MS × MS (the isomers were differentiated by the statistical/chemometric analysis of the fragment ions). − However, the separation resolution of LC is sometimes insufficient and is not suitable for comprehensive analysis of unknown samples since the target analyte should be decided before measuring the sample.…”

Section: Introductionmentioning

confidence: 99%

Comprehensive Analysis of Analogues of Amine-Related Psychoactive Substances Using Femtosecond Laser Ionization Mass Spectrometry

Madunil

Imasaka

2021

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Amine-related psychoactive molecules contain N–Cα and Cα–Cβ bonds, which easily dissociate to form various fragment ions in electron ionization mass spectrometry (EIMS). Therefore, observing a molecular ion and then determining the molecular weight of the analyte is difficult. In this study, we examined phenethylamine, 3,4-methylenedioxyphenethylamine, tryptamine, N-methylephedrine, and nicotine as well as analogues of amine-related psychoactive substances using EIMS and femtosecond laser ionization mass spectrometry (fs-LIMS) combined with gas chromatography for comprehensive analysis. A molecular ion was clearly observed in fs-LIMS for all of these compounds, which was in contrast to EIMS providing fragment ions dominantly (no molecular ion was observed for N-methylephedrine). This favorable result was obtained by adjusting the laser wavelength to the optimal value for two-photon ionization to minimize the excess energy remaining in the molecular ion. It therefore appears that fs-LIMS is superior to EIMS in terms of observing a molecular ion and would be potentially useful for identifying a variety of amine-related psychoactive substances, some of which are illegal and are of interest in the field of forensic science.

show abstract

Differentiation of FUB-JWH-018 positional isomers by electrospray ionization–triple quadrupole mass spectrometry

Cited by 6 publications

References 4 publications

Characteristics of ionization behaviors of aminonitrotoluene isomers produced by atmospheric pressure chemical ionization

Characteristics of ionization behaviors of aminonitrotoluene isomers produced by atmospheric pressure chemical ionization

Differentiation of Positional Isomers of Halogenated Benzoylindole Synthetic Cannabinoid Derivatives in Serum by Hybrid Quadrupole/Orbitrap Mass Spectrometry

Comprehensive Analysis of Analogues of Amine-Related Psychoactive Substances Using Femtosecond Laser Ionization Mass Spectrometry

Contact Info

Product

Resources

About