GC–MS and GC–IRD studies on dimethoxyamphetamines (DMA): Regioisomers related to 2,5-DMA

Maher, Hadir M.; Awad, Tamer; DeRuiter, Jack; Clark, Charles R.

doi:10.1016/j.forsciint.2009.08.010

Cited by 19 publications

(24 citation statements)

References 22 publications

(34 reference statements)

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“…The elution order was the same for the underivatized and all derivatized dimethoxybenzylpiperazines evaluated in this project. Previous studies on the isomeric dimethoxyphenethylamines and the dimethoxyamphetamines showed an identical elution order to that observed in this study. The chromatographic separation for the compounds shown in Figure is less than ideal with non‐baseline resolution obtained for the two 1,2,3‐trisubstituted aromatic systems (Compounds 1 and 4) as well as the later elution pair, Compounds 5 and 6.…”

Section: Resultssupporting

confidence: 87%

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GC‐MS and GC‐IRD studies on the six‐ring regioisomeric dimethoxybenzylpiperazines (DMBPs)

Abdel‐Hay

DeRuiter

Clark

2012

Drug Testing and Analysis

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Gas chromatography with infrared detection (GC-IRD) provides direct confirmatory data for the differentiation between the six regioisomeric aromatic ring substituted dimethoxybenzylpiperazines (DMBPs). These regioisomeric substances are resolved by GC and the vapour-phase infrared spectra clearly differentiate among the six dimethoxybenzyl substitution patterns. The mass spectra for these regioisomeric substances are almost identical. With only the 2,3-dimethoxy isomer showing one unique major fragment ion at m/z 136. Thus mass spectrometry does not provide for the confirmation of identity of any one of these compounds to the exclusion of the other isomers. Perfluoroacylation of the secondary amine nitrogen for each of the six regioisomers gave mass spectra showing some differences in the relative abundance of fragment ions without the appearance of any unique fragments for specific confirmation of structure. Gas chromatography coupled with time-of-flight mass spectrometric detection (GC-TOF) provided an additional means of confirmation of the elemental composition of the major fragment ions in the mass spectra of these compounds.

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Section: Resultssupporting

confidence: 87%

“…This fragment occurs in all the mass spectra of the underivatized and TFA, PFPA and HFBA derivatives of the ortho‐methoxy DMBPs. This suggested mechanism for the loss of CH 2 O from the ortho‐methoxy benzyl cations was previously discussed …”

Section: Resultssupporting

confidence: 54%

GC‐MS and GC‐IRD studies on the six‐ring regioisomeric dimethoxybenzylpiperazines (DMBPs)

Abdel‐Hay

DeRuiter

Clark

2012

Drug Testing and Analysis

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“…), are the most studied and described in the literature. Most popular phenethylamines contain methoxy groups in positions 2 and 5 and different lipophilic substituents in position 4 in benzene ring (2C family) …”

Section: Introductionmentioning

confidence: 99%

“…Applying GC/MS to study amphetamines of 2C and NBOMe series (as well as of the metabolites thereof) and to ensure their reliable determination and identification, their acyl and alkyl derivatives are often obtained …”

Section: Introductionmentioning

confidence: 99%

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

et al. 2016

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Emergence of new psychoactive substances, hallucinogenic phenethylamines in particular, in illicit market is a serious threat to human health in global scale. We have detected and identified N-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new compound in NBOMe series. Identification was achieved by means of gas chromatography/mass spectrometry (GC/MS), including high-resolution mass spectrometry with tandem experiments (GC/HRMS and GC/HRMS ), ultra-high performance liquid chromatography/high-resolution mass spectrometry with tandem experiments (UHPLC/HRMS and UHPLC/HRMS ), and H and C nuclear magnetic resonance spectroscopy. The peculiarities of fragmentation of the compound under electron ionization (EI) and collision-induced dissociation were studied. Despite of the empirical rule denying migration of the hydrogen atom in McLafferty rearrangement to the benzene ring with substituents in the both ortho-positions, it easily occurs for 2,4,6-TMPEA-NBOMe in EI conditions. We have noticed that electron-donating substituents, e.g. methoxy groups in the both ortho-positions and para-positions favor the rearrangement. For specially synthesized N-methyl and N-acyl derivatives McLafferty rearrangement is not observed. N-Acyl derivatives demonstrate McLafferty rearrangement, but the charge retains at the alternative fragment involving N-acyl carbonyl group. We have also showed that the hydrogen atoms in 2,4,6-trimethoxybenzene ring may be easily substituted for deuterium or for strong electrophiles like trifluoroacetyl. Analytical characteristics of 2,4,6-TMPEA-NBOMe and of some derivatives thereof which enable their determination in various criminal seizures are given. Copyright © 2016 John Wiley & Sons, Ltd.

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“…In the past, several analytical methods were established to quantify illegal drugs, including phenethylamines and their analogs. Most of these were based on GC–MS, LC–MS, or CE–MS 5–10. Although these methods, which enable us to confirm the molecular weight and to obtain structural information of the drugs, are excellent for the determination of phenethylamines, the analytical system, including the mass spectrometer, is extremely expensive, and cannot be used in many laboratories.…”

Section: Introductionmentioning

confidence: 99%

HPLC enantioseparation of α,α‐diphenyl‐2‐pyrrolidinemethanol and methylphenidate using a chiral fluorescent derivatization reagent and its application to the analysis of rat plasma

Inagaki¹,

Taniguchi²,

Hirashima³

et al. 2010

J of Separation Science

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Enantioseparation of α,α-diphenyl-2-pyrrolidinemethanol (D2PM) and methylphenidate (MPH; Ritalin(®)) using (R)-(-)-4-(N,N-dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole as the chiral derivatization reagent has been achieved for the first time, and a simple, reliable detection method using HPLC with fluorescence detection has been developed. D2PM and MPH have been derivatized with (R)-(-)-4-(N,N-dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole at 55°C for 15 min. The derivatives of D2PM and MPH have been separated, completely and rapidly, using a reversed-phase system within 16 min (resolution factor (R(s))=1.60 and 2.53, respectively). The detection limits of (R)- and (S)-D2PM were found to be 6.8 and 13 ng/mL, respectively, and those of D- and L-threo-MPH were 61 and 66 ng/mL, respectively (S/N=3). The proposed method was successfully applied to the analysis of rat plasma, where the rats were separately dosed with D2PM and MPH (Ritalin).

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GC–MS and GC–IRD studies on dimethoxyamphetamines (DMA): Regioisomers related to 2,5-DMA

Cited by 19 publications

References 22 publications

GC‐MS and GC‐IRD studies on the six‐ring regioisomeric dimethoxybenzylpiperazines (DMBPs)

GC‐MS and GC‐IRD studies on the six‐ring regioisomeric dimethoxybenzylpiperazines (DMBPs)

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

HPLC enantioseparation of α,α‐diphenyl‐2‐pyrrolidinemethanol and methylphenidate using a chiral fluorescent derivatization reagent and its application to the analysis of rat plasma

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