Identification and structural characterization of four novel synthetic cathinones: α-methylaminohexanophenone (hexedrone, HEX), 4-bromoethcathinone (4-BEC), 4-chloro-α-pyrrolidinopropiophenone (4-Cl-PPP), and 4-bromo-α-pyrrolidinopentiophenone (4-Br-PVP) after their seizures

Błażewicz, Agata; Bednarek, Elżbieta; Sitkowski, Jerzy; Popławska, Magdalena; Stypulkowska, K.; Bocian, Wojciech; Kozerski, Lech

doi:10.1007/s11419-017-0360-2

Cited by 19 publications

(28 citation statements)

References 20 publications

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“…Mass spectrometric techniques can be successfully used for the identification of synthetic cathinones. The electron ionization (EI) mass spectra of these compounds show no molecular ions; thus, high‐performance liquid electrospray/electrospray ionization mass spectrometry (HPLC/ESI‐MS) seems to be a much better technique than gas chromatography/EI‐MS for their identification . Well documented in the literature, the fragmentation pathways of [M + H] + ions (generated by ESI‐MS) of synthetic cathinones may be useful for their identification …”

Section: Methodsmentioning

confidence: 99%

“…The electron ionization (EI) mass spectra of these compounds show no molecular ions; thus, high-performance liquid electrospray/electrospray ionization mass spectrometry (HPLC/ESI-MS) seems to be a much better technique than gas chromatography/EI-MS for their identification. [6][7][8][9][10] Well documented in the literature, the fragmentation pathways of [M + H] + ions (generated by ESI-MS) of synthetic cathinones may be useful for their identification. [11][12][13][14][15][16][17][18][19][20][21] The only fragmentation pathway that, in our opinion, has not been properly described is the mechanism of the loss of a water molecule from [M + H] + ions.…”

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confidence: 99%

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The mechanism of water loss from protonated cathinones

Frański

Gierczyk

Kasperkowiak

et al. 2020

Rapid Comm Mass Spectrometry

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

The mechanism of water loss from protonated cathinones

Frański

Gierczyk

Kasperkowiak

et al. 2020

Rapid Comm Mass Spectrometry

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“…As described above, α-PPs have a tertiary amine structure and do not produce a dehydrated product ion. [6][7][8][9]16,17,19,20 However, dehydrated ions are generated from the two major metabolites of α-PPs, the 1-OH and 2 00 -oxo. [6][7][8][9]19,20 In this section, the dehydration mechanism of the metabolites of α-PBP, 1-OH-α-PBP, and 2 00 -oxo-α-PBP ( Figure 1B) was examined and discussed.…”

Section: Generation Of Dehydrated Ions From the Main Metabolites Ofmentioning

confidence: 99%

“…Dehydrated ions have been observed from both primary and secondary amine structures such as 3,4-dimethylcathinone, methcathinone, 3,4-dimethylmethcathinone, N-propylcathinone, hexedrone, and ethylone, [10][11][12][13][14][15][16][17][18] whereas tertiary amine structures such as 4-chloro-N,N-dimethylcathinone and α-pyrrolidinophenones (α-PPs) do not generate the dehydration ion. [6][7][8][9][14][15][16][17][18][19][20] Thus, the dehydrated ions can possibly be used for the structural identification of CATs, regardless of the substituents on the benzene ring and/or the alkyl chain length.…”

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Dehydration‐fragmentation mechanism of cathinones and their metabolites in ESI‐CID

et al. 2020

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Various cathinone‐derived designer drugs (CATs) have recently appeared on the drug market. This study examined the mechanism for the generation of dehydrated ions for CATs during electrospray ionization collision‐induced dissociation (ESI‐CID). The generation mechanism of dehydrated ions is dependent on the amine classification in the cathinone skeleton, which is used in the identification of CATs. The two hydrogen atoms eliminated during the dehydration of cathinone (primary amine) and methcathinone (secondary amine) were determined, and the reaction mechanism was elucidated through the deuterium labeling experiments. The hydrogen atom bonded to the amine nitrogen was eliminated with the proton added during ESI, in both of the tested compounds. This provided evidence that CATs with tertiary amine structures (such as dimethylcathinone and α‐pyrrolidinophenones [α‐PPs]) do not undergo dehydration. However, it was shown that the two major tertiary amine metabolites (1‐OH and 2″‐oxo) of CATs generate dehydrated ions in ESI‐CID. The dehydration mechanisms of the metabolites of α‐pyrrolidinobutiophenone (α‐PBP) belongs to α‐PPs were also investigated. Stable‐isotope labeling showed the dehydration of the 1‐OH metabolite following a simple mechanism where the hydroxy group was eliminated together with the proton added during ESI. In contrast, the dehydration mechanism of the 2″‐oxo metabolite involved hydrogen atoms in three or more locations along with the carbonyl group oxygen, indicating that dehydration occurred via multiple mechanisms likely including the rearrangement reaction of hydrogen atoms. These findings presented herein indicate that the dehydrated ions in ESI‐CID can be used for the structural identification of CATs.

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“…Five consecutive amendments of the Act on Counteracting Drug Addiction (ACDA) in Poland resulted in controlling over 150 NPSs. Details of the legislation of NPSs until 2015 in Poland were described in our previous paper [5]. Until the end of 2017 (the reporting period), many novel cathinones were not included in the ACDA.…”

Section: Introductionmentioning

confidence: 99%

Identification and structural characterization of synthetic cathinones: N-propylcathinone, 2,4-dimethylmethcathinone, 2,4-dimethylethcathinone, 2,4-dimethyl-α-pyrrolidinopropiophenone, 4-bromo-α-pyrrolidinopropiophenone, 1-(2,3-dihydro-1H-inden-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one and 2,4-dimethylisocathinone

et al. 2019

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Purpose Seven synthetic cathinone derivatives detected in samples seized in Poland from clandestine laboratories: N-propylcathinone, 2,4-dimethylmethcathinone (2,4-DMMC), 2,4-dimethylethcathinone (2,4-DMEC), 2,4-dimethyl-αpyrrolidinopropiophenone (2,4-DMPPP) and 2,4-dimethylisocathinone (4-iso-DMC), collected from smartshops: 4-bromoα-pyrrolidinopropiophenone (4-Br-PPP) or received from an attorney 1-(2,3-dihydro-1H-inden-5-yl)-2-(pyrrolidin-1-yl) hexan-1-one (5-BPDi) were identified and analytically characterized. Methods Unequivocal identification of seven cathinones was performed using liquid chromatography-high-resolution tandem mass spectrometry with a quadrupole time-of-flight analyzer, gas chromatography with mass spectrometry and nuclear magnetic resonance spectroscopy. Results In this study, we reported the detection and structure elucidation of seven substituted cathinones: N-propylcathinone, 2,4-DMMC, 2,4-DMEC, 2,4-DMPPP, 4-Br-PPP, 5-BPDi and 2,4-iso-DMC. Conclusions New derivatives of cathinone still appear on the market, mainly due to their legal status. This situation clearly indicates and alarms that permanent recognition of the designer drug market should be conducted. To the best of our knowledge, this is the first comprehensive report to fully characterize these cathinones; however, some analytical data have been published recently.

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Identification and structural characterization of four novel synthetic cathinones: α-methylaminohexanophenone (hexedrone, HEX), 4-bromoethcathinone (4-BEC), 4-chloro-α-pyrrolidinopropiophenone (4-Cl-PPP), and 4-bromo-α-pyrrolidinopentiophenone (4-Br-PVP) after their seizures

Cited by 19 publications

References 20 publications

The mechanism of water loss from protonated cathinones

The mechanism of water loss from protonated cathinones

Dehydration‐fragmentation mechanism of cathinones and their metabolites in ESI‐CID

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