New “party pill” components in New Zealand: The synthesis and analysis of some β-ketone analogues of 3,4-methylenedioxymethamphetamine (MDMA) including βk-DMBDB (β-ketone-N,N-dimethyl-1-(1,3-benzodioxol-5-yl)-2-butanamine)

Russell, Matthew; Bogun, Ben

doi:10.1016/j.forsciint.2011.03.005

Cited by 20 publications

(21 citation statements)

References 2 publications

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“…The EI‐MS is shown in Figure 11 and is consistent with previously reported data 7, 8. Consistent with other synthetic cathinones, the molecular ion ( m / z 221) is weak and the base peak ( m / z 72) corresponds to the formation of an iminium ion (C 4 H 10 N + ).…”

Section: Resultssupporting

confidence: 91%

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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Section: Resultssupporting

confidence: 91%

Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

Maheux

Alarcon

Copeland

et al. 2015

Drug Testing and Analysis

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“…[20][21][22][23] These include electrochemistry 24 and the use of SERS Raman spectroscopy studied by both Mabbott et al 25,26 and ourselves, 27 in addition to the traditional chromatographic mass spectrometric techniques. [29][30][31][32][33][34][35][36][37] The majority of the seized derivatized cathinone materials are assumed to be racemic, although there has not been a systematic study to demonstrate this. 6,7 Studies have now shown that a wide range of cathinone derivatives can be reliably obtained using a synthetic pathway initially reported in 1950 28 via the acid-catalyzed bromination of the appropriate aryl ketone, followed by amination to give the target as a racemic product.…”

Section: Introductionmentioning

confidence: 99%

Isolation and structural determination of non-racemic tertiary cathinone derivatives

et al. 2015

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The racemic tertiary cathinones N,N-dimethylcathinone (1), N,N-diethylcathinone (2) and 2-(1-pyrrolidinyl)-propiophenone (3) have been prepared in reasonable yield and characterized using NMR and mass spectroscopy. HPLC indicates that these compounds are isolated as the anticipated racemic mixture. These can then be co-crystallized with (+)-O,O′-di-p-toluoyl-D-tartaric, (+)-O,O′-dibenzoyl-D-tartaric and (−)-O,O′-dibenzoyl-L-tartaric acids giving the single enantiomers S and R respectively of 1, 2 and 3, in the presence of sodium hydroxide through a dynamic kinetic resolution. X-ray structural determination confirmed the enantioselectivity. The free amines could be obtained following basification and extraction. In methanol these are reasonably stable for the period of several hours, and their identity was confirmed by HPLC and CD spectroscopy.

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“…A c c e p t e d M a n u s c r i p t 5 In order to evade controlled substance statutes -which are usually written very specifically with respect to the substance under control -"designer" phenethylamines and cathinones are typically crafted by replacing phenyl ring hydrogens with various substituents.…”

Section: Page 5 Of 36mentioning

confidence: 99%

“…Phenethylamines are substances structurally related to phenethylamine or amphetamine; whereas, cathinones are β-keto-phenethylamines structurally related to cathinone or other naturally occurring alkaloids [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Regioisomeric and enantiomeric analyses of 24 designer cathinones and phenethylamines using ultra high performance liquid chromatography and capillary electrophoresis with added cyclodextrins

Li¹,

Lurie²

2015

Forensic Science International

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New “party pill” components in New Zealand: The synthesis and analysis of some β-ketone analogues of 3,4-methylenedioxymethamphetamine (MDMA) including βk-DMBDB (β-ketone-N,N-dimethyl-1-(1,3-benzodioxol-5-yl)-2-butanamine)

Cited by 20 publications

References 2 publications

Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

Isolation and structural determination of non-racemic tertiary cathinone derivatives

Regioisomeric and enantiomeric analyses of 24 designer cathinones and phenethylamines using ultra high performance liquid chromatography and capillary electrophoresis with added cyclodextrins

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