The analysis of substituted cathinones. Part 3. Synthesis and characterisation of 2,3-methylenedioxy substituted cathinones

Kavanagh, Pierce V.; O’Brien, John E.; Fox, John L.; O'Donnell, Cora; Christie, Rachel; Power, John D.; McDermott, Seán D.

doi:10.1016/j.forsciint.2011.08.011

Cited by 52 publications

(53 citation statements)

References 8 publications

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“…[18] For example, FT-IR was used to discriminate between three different trifluoromethylmethcathinone analogues [18] and two methylenedioxypyrovalerone (MDPV) isomers. [26] Although FT-IR can be used in the solid-state, analysis through packaging is often difficult and interferences from excipients/cutting agents are common. The use of NIR spectroscopy for the identification of NPS also shows promise, [27,28] but NIR is more susceptible to moisture effects, physical properties and cutting agents, and often requires careful selection of data treatment.…”

Section: Introductionmentioning

confidence: 99%

Identification of new psychoactive substances (NPS) using handheld Raman spectroscopy employing both 785 and 1064 nm laser sources

Guirguis

Girotto

Berti

et al. 2017

Forensic Science International

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The chemical identification of new psychoactive substances (NPS) in the field is challenging due not only to the plethora of substances available, but also as a result of the chemical complexity of products and the chemical similarity of NPS analogues. In this study, handheld Raman spectroscopy and the use of two excitation wavelengths, 785 and 1064 nm, were evaluated for the identification of 60 NPS products. The products contained a range of NPS from classes including the aminoindanes, arylalkylamines, benzodiazepines, and piperidines & pyrrolidines. Identification was initially assessed using the instruments' in built algorithm (i.e., % HQI) and then further by visual inspection of the Raman spectra. Confirmatory analysis was preformed using gas chromatography mass spectrometry. For the 60 diverse products, an NPS was successfully identified via the algorithm in 11 products (18 %) using the 785 nm source and 29 products (48 %) using the 1064 nm source. Evaluation of the Raman spectra showed that increasing the excitation wavelength from 785 to 1064 nm improved this 'first pass' identification primarily due to a significant reduction in fluorescence, which increased S/N of the characteristic peaks of the substance identified. True positive correlations between internet products and NPS signatures ranged from 57.0 to 91.3 % HQI with typical RSDs < 10 %. Tablet formulations and branded products were particularly challenging as a result of low NPS concentration and high chemical complexity, respectively. This study demonstrates the advantage of using a 1064 nm source with handheld Raman spectroscopy for improved 'first pass' NPS identification when minimal spectral processing is required, such as when working in field. Future investigations will focus on the use of mixture algorithms, effect of NPS concentration, and further improvement of spectral libraries.

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Section: Introductionmentioning

confidence: 99%

Identification of new psychoactive substances (NPS) using handheld Raman spectroscopy employing both 785 and 1064 nm laser sources

Guirguis

Girotto

Berti

et al. 2017

Forensic Science International

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show abstract

“…Infrared spectroscopy has been used to distinguish cathinone homologues6, 7, 12 and to differentiate cathinone regioisomers 28, 29. Similarly, Raman spectroscopy has been used for the identification and characterization of cathinones30 and their mono‐substituted and methylenedioxy substituted regioisomers 31.…”

Section: Resultsmentioning

confidence: 99%

Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

Maheux

Alarcon

Copeland

et al. 2015

Drug Testing and Analysis

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Ethylone, a synthetic cathinone with psychoactive properties, is a designer drug which has appeared on the recreational drug market in recent years. Since 2012, illicit shipments of ethylone hydrochloride have been intercepted with increasing frequency at the Canadian border. Analysis has revealed that ethylone hydrochloride exists as two distinct polymorphs. In addition, several minor impurities were detected in some seized exhibits. In this study, the two conformational polymorphs of ethylone hydrochloride have been synthesized and fully characterized by FTIR, FT‐Raman, powder XRD, GC‐MS, ESI‐MS/MS and NMR (13C CPMAS, 1H, 13C). The two polymorphs can be distinguished by vibrational spectroscopy, solid‐state nuclear magnetic resonance spectroscopy and X‐ray diffraction. The FTIR data are applied to the identification of both polymorphs of ethylone hydrochloride (mixed with methylone hydrochloride) in a laboratory submission labelled as 'Ocean Snow Ultra’. The data presented in this study will assist forensic scientists in the differentiation of the two ethylone hydrochloride polymorphs. This report, alongside our recent article on the single crystal X‐ray structure of a second polymorph of this synthetic cathinone, is the first to confirm polymorphism in ethylone hydrochloride. © 2015 Canada Border Services Agency. Drug Testing and Analysis published by John Wiley & Sons, Ltd. © 2015 Canada Border Services Agency. Drug Testing and Analysis published by John Wiley & Sons, Ltd.

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“…Methylone (3,4-MDMC, Fig. 1d), is a widely abused cathinone commonly found as an active ingredient in seized bath salt mixtures [14,34,35]. The other three cathinones are methylone structural variants (i.e.…”

Section: Resultsmentioning

confidence: 99%

“…Many of the known cathinone analogs are isomers which vary only in the relative position of the aromatic ring substituent, such as is the case for 2,3-MDMC and 3,4-MDMC. Therefore, the combination of GC-MS, which would yield isomer retention time and minimal structural information [35,36], and DART-TOF-MS with CID, which would provide detailed structural information including both the molecular ion and product fragments with high mass accuracy, would be extremely powerful in providing a complete picture of the constituents of a sample of interest.…”

Section: High Mass Accuracy For Preliminary Determination Of Unknownsmentioning

confidence: 99%

DART–MS in-source collision induced dissociation and high mass accuracy for new psychoactive substance determinations

Musah

Cody

Domin

et al. 2014

Forensic Science International

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The analysis of substituted cathinones. Part 3. Synthesis and characterisation of 2,3-methylenedioxy substituted cathinones

Cited by 52 publications

References 8 publications

Identification of new psychoactive substances (NPS) using handheld Raman spectroscopy employing both 785 and 1064 nm laser sources

Identification of new psychoactive substances (NPS) using handheld Raman spectroscopy employing both 785 and 1064 nm laser sources

Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

DART–MS in-source collision induced dissociation and high mass accuracy for new psychoactive substance determinations

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