Identification and analytical characterization of N‐propyl norbutylone, N‐butyl norbutylone, N‐benzyl norheptedrone, and N‐pyrrolidinyl‐3,4‐DMA

Liu, Cui‐mei; Hua, Zhendong; Song, Chun‐hui; Wang, Jia

doi:10.1002/dta.3358

Cited by 6 publications

(3 citation statements)

References 13 publications

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“…21 EIEIO has also been applied to the characterization of new psychoactive substances (NPS), which generated only one product ion in the CID mode. 22 In general, EIEIO provides additional fragmentation information that complements the CID, aiding in structure elucidation. Furthermore, to the best of our knowledge, there is no global metabolome annotation for EIEIO-untargeted metabolomics data due to the lack of reference EIEIO MS/MS databases.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Besides, combined with differential mobility spectrometry (DMS), EIEIO can differentiate constitutional isomers, cis/trans isomers, and diastereomers of eicosanoids . EIEIO has also been applied to the characterization of new psychoactive substances (NPS), which generated only one product ion in the CID mode . In general, EIEIO provides additional fragmentation information that complements the CID, aiding in structure elucidation.…”

Section: Introductionmentioning

confidence: 99%

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Enhancing Metabolome Annotation by Electron Impact Excitation of Ions from Organics-Molecular Networking

Wang,

Sun,

Wang

et al. 2024

Anal. Chem.

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Liquid chromatography−high-resolution mass spectrometry (LC−HRMS) is widely used in untargeted metabolomics, but large-scale and high-accuracy metabolite annotation remains a challenge due to the complex nature of biological samples. Recently introduced electron impact excitation of ions from organics (EIEIO) fragmentation can generate information-rich fragment ions. However, effective utilization of EIEIO tandem mass spectrometry (MS/MS) is hindered by the lack of reference spectral databases. Molecular networking (MN) shows great promise in large-scale metabolome annotation, but enhancing the correlation between spectral and structural similarity is essential to fully exploring the benefits of MN annotation. In this study, a novel approach was proposed to enhance metabolite annotation in untargeted metabolomics using EIEIO and MN. MS/MS spectra were acquired in EIEIO and collision-induced dissociation (CID) modes for over 400 reference metabolites. The study revealed a stronger correlation between the EIEIO spectra and metabolite structure. Moreover, the EIEIO spectral network outperformed the CID spectral network in capturing structural analogues. The annotation performance of the structural similarity network for untargeted LC−MS/MS was evaluated. For the spiked NIST SRM 1950 human plasma, the annotation coverage and accuracy were 72.94 and 74.19%, respectively. A total of 2337 metabolite features were successfully annotated in NIST SRM 1950 human plasma, which was twice that of LC−CID MS/MS. Finally, the developed method was applied to investigate prostate cancer. A total of 87 significantly differential metabolites were annotated. This study combining EIEIO and MN makes a valuable contribution to improving metabolome annotation.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enhancing Metabolome Annotation by Electron Impact Excitation of Ions from Organics-Molecular Networking

Wang,

Sun,

Wang

et al. 2024

Anal. Chem.

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show abstract

“…In recent years, new psychoactive substances (NPS) are continuing to emerge in the form of stand-alone compounds or mixtures and are gradually replacing traditional drugs as the dominant abuse drug in many countries [ 1 ]. Until 2021, the United Nations Office on Drugs and Crime (UNODC) has received reports from 133 countries and regions worldwide, documenting 1079 kinds of new psychoactive substances.…”

Section: Introductionmentioning

confidence: 99%

Study on the Mass Spectrometry Fragmentation Patterns for Rapid Screening and Structure Identification of Ketamine Analogues in Illicit Powders

Fan,

Gao,

Chen

et al. 2023

Molecules

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Ketamine analogues have been emerging in recent years and are causing severe health and social problems worldwide. Ketamine analogues use 2-phenyl-2-aminocyclohexanone as the basic structure and achieve physiological reactions similar to or even more robust than the prototype of ketamine by changing the substituents on the benzene ring (R1 and R2) and amine group (RN1). Therefore, the mass spectrometry (MS) fragmentation pathways and fragments of ketamine analogues have certain regularity. Eight ketamine analogues are systematically investigated by GC-QTOF/MS and LC-Q-Orbitrap MS/MS with the positive mode of electrospray ionization. The MS fragmentation patterns of ketamine analogues are summarized according to high-resolution MS data. The α-cleavage of carbon bond C1-C2 in the cyclohexanone moiety and further losses of CO, methyl radical, ethyl radical and propyl radical are the characteristic fragmentation pathways of ketamine analogues in EI-MS mode. The loss of H2O or the sequential loss of RN1NH2, CO and C4H6 are the distinctive fragmentation pathways of ketamine analogues in ESI-MS/MS mode. Moreover, these MS fragmentation patterns are first introduced for the rapid screening of ketamine analogues in suspicious powder. Furthermore, the structure of the ketamine analogue in suspicious powder is 2-(Methylamino)-2-(o-tolyl)cyclohexan-1-one, which is further confirmed by NMR. This study contributes to the identification of the chemical structure of ketamine analogues, which can be used for the rapid screening of ketamine analogues in seized chemicals.

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EMCDDA framework and practical guidance for naming cathinones

Pulver,

Fischmann,

Gallegos

et al. 2024

Drug Testing and Analysis

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Cathinones are often sold as “legal” alternatives to controlled stimulants such as amphetamine, MDMA and cocaine. Cathinones are the second largest group of new psychoactive substances (NPS), with close to 170 monitored by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). Although all cathinones are related to the parent compound cathinone, one of the psychoactive principles in khat, assigning consistent, informative and user‐friendly common names to these substances is challenging. Over time different naming approaches have been applied, leading to cathinones being known by several names. This work provides a framework and practical examples for the consistent naming of cathinones which is easy to understand and can be applied by the forensic community, researchers, clinical practitioners, and policy makers. The scope of the issue and rationale for earlier naming approaches are also discussed. The new naming framework has been developed based on established naming approaches and centered around the common “cathinone,” and “phenone” motifs/scaffolds. The proposed framework establishes clear rules to derive the EMCDDA framework names for cathinones. Each name is, in turn, composed by a principal name containing a parent letter, derived after the “cathinone” or the “phenone” scaffold. Additional substitutions are prepended to the principal name. The framework also provides for exceptions for several cathinones and structural analogs scheduled under UN and EU legislation.

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Identification and analytical characterization of N‐propyl norbutylone, N‐butyl norbutylone, N‐benzyl norheptedrone, and N‐pyrrolidinyl‐3,4‐DMA

Cited by 6 publications

References 13 publications

Enhancing Metabolome Annotation by Electron Impact Excitation of Ions from Organics-Molecular Networking

Enhancing Metabolome Annotation by Electron Impact Excitation of Ions from Organics-Molecular Networking

Study on the Mass Spectrometry Fragmentation Patterns for Rapid Screening and Structure Identification of Ketamine Analogues in Illicit Powders

EMCDDA framework and practical guidance for naming cathinones

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