Can NMR spectroscopy discriminate between NPS amphetamines and cathinones? An evaluation by in silico studies and chemometrics

Rodrigues, Caio Henrique Pinke; Leite, Vitor B. P.; Bruni, Aline Thais

doi:10.1016/j.chemolab.2021.104265

Cited by 11 publications

(5 citation statements)

References 102 publications

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“…Considering the lack of information about these substances and the costs of analysis, structure, and human resources involved in obtaining spectroscopic data, DFT methods linked to unsupervised analysis were able to give insights about each group's spectroscopic behavior, providing a viable alternative to acquiring data and improving the knowledge for NPSs [90,114].…”

Section: Discussionmentioning

confidence: 99%

Evaluation of Density Functional Theory-Generated Data for Infrared Spectroscopy of Novel Psychoactive Substances Using Unsupervised Learning

dos Santos,

Bruni

2024

Psychoactives

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Novel psychoactive substances (NPSs) are compounds plotted to modify the chemical structures of prohibited substances, offering alternatives for consumption and evading legislation. The prompt emergence of these substances presents challenges in health concerns and forensic assessment because of the lack of analytical standards. A viable alternative for establishing these standards involves leveraging in silico methods to acquire spectroscopic data. This study assesses the efficacy of utilizing infrared spectroscopy (IRS) data derived from density functional theory (DFT) for analyzing NPSs. Various functionals were employed to generate infrared spectra for five distinct NPS categories including the following: amphetamines, benzodiazepines, synthetic cannabinoids, cathinones, and fentanyls. PRISMA software was conceived to rationalize data management. Unsupervised learning techniques, including Hierarchical Cluster Analysis (HCA), Principal Component Analysis (PCA), and t-distributed stochastic neighbor embedding (t-SNE), were utilized to refine the assessment process. Our findings reveal no significant disparities among the different functionals used to generate infrared spectra data. Additionally, the application of unsupervised learning demonstrated adequate segregation of NPSs within their respective groups. In conclusion, integrating theoretical data and dimension reduction techniques proves to be a powerful strategy for evaluating the spectroscopic characteristics of NPSs. This underscores the potential of this combined methodology as a diagnostic tool for distinguishing IR spectra across various NPS groups, facilitating the evaluation of newly unknown compounds.

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Section: Discussionmentioning

confidence: 99%

Evaluation of Density Functional Theory-Generated Data for Infrared Spectroscopy of Novel Psychoactive Substances Using Unsupervised Learning

dos Santos,

Bruni

2024

Psychoactives

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“…Density functional theory (DFT) has been used to predict the infrared spectra of phenylethylamines with good success (Graf et al, 2020). DFT has also been used to model NMR shifts for amphetamines and cathinones (Rodrigues et al, 2021). Other approaches have been developed to identify new substances using chemometrics for both GC-EI-MS (Moorthy et al, 2020) and Raman spectroscopy (Calvo-Castro et al, 2018).…”

Section: Data-centric Solutionsmentioning

confidence: 99%

Forensic seized drug analysis: Current challenges and emerging analytical solutions

Sisco

2023

WIREs Forensic Science

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Over the past decade, new challenges in seized drug analysis have pushed the limits of existing instrumentation and workflows. These challenges include increasing caseloads, complex samples containing previously unidentified substances, and evolving legal requirements. Traditional approaches to seized drug analysis—such as gas chromatography mass spectrometry, color tests, and Fourier transform infrared spectroscopy—can be insufficient for current challenges, motivating the community to explore new instrumentation or data analysis solutions. However, the road to validation, implementation, and adoption of new technologies and solutions can be arduous. In this overview, we discuss the major challenges facing the seized drug community that can be addressed by advances in analytical approaches and highlight some emerging techniques that have been or could be adopted by laboratories in the near‐term. We also discuss specific hurdles limiting the implementation and adoption of new techniques, and approaches to lower these barriers.This article is categorized under: Forensic Chemistry and Trace Evidence > Controlled and Emerging Drug Compounds Forensic Chemistry and Trace Evidence > Emerging Technologies and Methods Forensic Chemistry and Trace Evidence > Presentation and Evaluation of Forensic Science Output

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“…Development of computational resources rendered quantum-chemical calculations of To obtain additional confirmation of the oxime double bond geometry, DFT calculations of NMR chemical shifts for Eand Z-isomers of IQ-1 and Trp-Ox were carried out. Development of computational resources rendered quantum-chemical calculations of NMR spectral parameters a powerful tool for establishing the structures of organic compounds, including complex natural products [72][73][74][75] and even stereoisomers [76,77].…”

Section: Iq-1mentioning

confidence: 99%

Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime

et al. 2023

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11H-Indeno[1,2-b]quinoxalin-11-one oxime (IQ-1) and tryptanthrin-6-oxime are potent c-Jun N-terminal kinase 3 (JNK-3) inhibitors demonstrating neuroprotective, anti-inflammatory and anti-arthritic activity. However, the stereochemical configuration of the oxime carbon–nitrogen double bond (E- or Z-) in these compounds was so far unknown. In this contribution, we report the results of the determination of the double bond configuration in the solid state by single crystal X-ray diffraction and in solution by 1D and 2D NMR techniques and DFT calculations. It was found that both in the solid state and in solution, IQ-1 adopts the E-configuration stabilized by intermolecular hydrogen bonds, in contrast to previously assumed Z-configuration that could be stabilized only by an intramolecular hydrogen bond.

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Can NMR spectroscopy discriminate between NPS amphetamines and cathinones? An evaluation by in silico studies and chemometrics

Cited by 11 publications

References 102 publications

Evaluation of Density Functional Theory-Generated Data for Infrared Spectroscopy of Novel Psychoactive Substances Using Unsupervised Learning

Evaluation of Density Functional Theory-Generated Data for Infrared Spectroscopy of Novel Psychoactive Substances Using Unsupervised Learning

Forensic seized drug analysis: Current challenges and emerging analytical solutions

Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime

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