Proton and carbon-13 NMR assignments of 3,4-methylenedioxyamphetamine (MDA) and some analogues of MDA

Cason, Terry A. Dal; Meyers, John A.; Lankin, David C.

doi:10.1016/s0379-0738(97)02102-6

Cited by 7 publications

(4 citation statements)

References 8 publications

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“…The solid was then washed with cooled acetone and dried under vacuum to reveal white or beige MDMA·HCl (0.33 g, 94% yield). IR, 1 H NMR, and 13 C NMR analysis of synthesized compounds was in agreement with published data reported previously; ,− see the Supporting Information (SI).…”

Section: Methodssupporting

confidence: 89%

Role of Five Synthetic Reaction Conditions on the Stable Isotopic Composition of 3,4-Methylenedioxymethamphetamine

et al. 2010

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The identification of links between seizures of illicit 3,4-methylenedioxymethamphetamine (MDMA or "ecstasy") has been a global target of law enforcement agencies in recent years. Previous work has shown that, when the reaction conditions are carefully repeated from batch to batch, stable isotope ratios allow the discrimination of MDMA.HCl batches according to synthetic route used for manufacture. In this study, the effects of altering five reaction conditions relating to the Pt/H(2) reductive amination synthesis were, for the first time, systematically investigated using a two level, five factor factorial design. Results indicate that the delta(2)H values of MDMA.HCl are affected by the length of imine stir time, and the delta(15)N values are affected by the degree of excess methylamine employed. Furthermore, the delta(13)C and delta(18)O values have been shown to be affected by the efficiency of the reaction, despite the similarity in carbon and oxygen composition of the starting material and product molecules. In addition to being of theoretical importance in this field of analytical science overall, this work is essential in order to more fully contextualize the interpretation of IRMS data which may be used as potential forensic evidence.

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Section: Methodssupporting

confidence: 89%

Role of Five Synthetic Reaction Conditions on the Stable Isotopic Composition of 3,4-Methylenedioxymethamphetamine

et al. 2010

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“…Analysis was in agreement with published data. 31,32 IR v max (CH 2 Cl 2 )/cm -1 : 1489, 1444, 1249 (C-O), 1041 (C-O), 938. 1 H NMR (400 MHz, CDCl 3 ): δ 1.05 (d, 3H, J 6.2 Hz, CH 3 ), 2.40 (s, 3H, NCH 3 ), 2.52 -2.65 (m, 2H, CH 2 ), 2.69 -2.77 (m, 1H, CH), 5.93 (s, 2H, OCH 2 O), 6.63 (dd, 1H, J 7.8 and 1.4 Hz, ArH), 6.68 (d, 1H J 1.5 Hz, ArH), 6.73 ppm (d, 1H, J 7.8 Hz, ArH).…”

Section: Methodsmentioning

confidence: 99%

Emerging Use of Isotope Ratio Mass Spectrometry as a Tool for Discrimination of 3,4-Methylenedioxymethamphetamine by Synthetic Route

et al. 2008

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Drug profiling, or the ability to link batches of illicit drugs to a common source or synthetic route, has long been a goal of law enforcement agencies. Research in the past decade has explored drug profiling with isotope ratio mass spectrometry (IRMS). This type of research can be limited by the use of substances seized by police, of which the provenance is unknown. Fortunately, however, some studies in recent years have been carried out on drugs synthesized in-house and therefore of known history. In this study, 18 MDMA samples were synthesized in-house from aliquots of the same precursor by three common reductive amination routes and analyzed for 13C, 15N, and 2H isotope abundance using IRMS. For these three preparative methods, results indicate that 2H isotope abundance data is necessary for discrimination by synthetic route. Furthermore, hierarchical cluster analysis using 2H data on its own or combined with 13C and/or 15N provides a statistical means for accurate discrimination by synthetic route.

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“…Amphetamines and related compounds have been analyzed by GC/FT-IR (165), HPLC/UV (166), negative-ion chemical ionization MS (167), capillary zone electrophoresis (CZE) (168), and CE and HPLC (169). Methlenedioxyamphetamines and related compounds have been characterized by GC/ MS (170), HPLC with fluorometric detection (171), LC and MS (172,173), GC/FID and GC/MS (174), ion trap MS (175), GC/ CIMS with derivatization (176), nuclear magnetic resonance (NMR) (177)(178)(179), and Fourier transform raman spectroscopy (FTRS) (180). Some unusually marked and single-scored tablets were analyzed for illicit drug content to yield 3,4-methylenedioxyethylamphetamine (181).…”

Section: Drugs and Poisonsmentioning

confidence: 99%

Forensic Science

Brettell¹,

Inman

Rudin

et al. 1999

Anal. Chem.

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Proton and carbon-13 NMR assignments of 3,4-methylenedioxyamphetamine (MDA) and some analogues of MDA

Cited by 7 publications

References 8 publications

Role of Five Synthetic Reaction Conditions on the Stable Isotopic Composition of 3,4-Methylenedioxymethamphetamine

Role of Five Synthetic Reaction Conditions on the Stable Isotopic Composition of 3,4-Methylenedioxymethamphetamine

Emerging Use of Isotope Ratio Mass Spectrometry as a Tool for Discrimination of 3,4-Methylenedioxymethamphetamine by Synthetic Route

Forensic Science

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