N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis

Brandt, Simon D.; Martins, Cláudia P.B.; Freeman, Sally; Dempster, Nicola M.; Wainwright, Mark; Riby, Philip; Alder, John F.

doi:10.1016/j.jpba.2007.12.024

Cited by 9 publications

(18 citation statements)

References 29 publications

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“…MS and CI-MS-MS mode as previously discussed in detail [13] and verification was obtained by synthesis which is reported here. The key EI-MS fragmentation steps for 3-(2-chloro/ bromoethyl)indoles and tetrahydro-b-carbolines (THBCs) are summarised in Fig.…”

Section: Gas Chromatography-mass Spectrometrymentioning

confidence: 79%

“…N-Chloromethyl-DMT chloride 2a has been reported previously [12,13]. N-Chloro-deuteromethyl-DMT chloride 2b (166 mg, 0.60 mmol, 55%), d 2 -DCM was used as solvent, and 2b was isolated as pale yellow needles: 1 …”

Section: General Procedures For the Synthesis Of N-halogenated-alkyl Dmentioning

confidence: 94%

“…Recent reports [12,13] indicated that DMT 1a was found to be sensitive to contact with dichloromethane (DCM), either during storage or short-term exposure during work-up which led to the identification of N-chloromethyl DMT chloride 2a (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…1). When 2a was subjected to gas chromatography-mass spectrometry (GC-MS) analysis however, rearrangements were observed instead which resulted in the absence of 2a and detection of 3-(2-chloroethyl)indole 3 and 2-methyltetrahydrob-carboline (2-Me-THBC) 4 in the total ion chromatograms [13] ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis

Brandt

Martins

Freeman

et al. 2008

Forensic Science International

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Section: Gas Chromatography-mass Spectrometrymentioning

confidence: 79%

Section: General Procedures For the Synthesis Of N-halogenated-alkyl Dmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis

Brandt

Martins

Freeman

et al. 2008

Forensic Science International

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“…Formaldehyde-adduct formation hindered the identification by electron ionization GC/MS. In literature, few reports were find concerning the condensation of a parent drug with the extraction solvent or contaminant, hindering the identification or leading to the misidentification by computer based library search [4][5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic characterization of 4-methylamphetamine: formaldehyde adduct formation hindered the identification by mass spectrometry

Coopman¹,

Delbeke²,

Ingelgem³

et al. 2012

Ann Toxicol Anal

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-A powder was submitted to the author's laboratory for analysis on the presence of illegal drugs. Based on the structure elucidation performed by nuclear nuclear magnetic resonance spectroscopy and analysis of the trimethylsilyl and trifluoroacetyl derivatives with gas chromatography mass spectrometry, the powder was found to contain the designer drugs 4-methylamphetamine, besides amphetamine and caffeine. The electron impact mass spectrum of 4-methylamphetamine obtained from the analysis of a methanolic sample solution showed a base ion of m/z 56 rather than the expected m/z 44, therefore no hit was found with an electron impact mass spectrum present in the mass spectral library and literature. The increase of 12 atomic mass units was explained by formaldehyde-adduct formation.Key words: 4-methylamphetamine, formaldehyde, mass spectrometry Résumé -Une poudre a été soumise au laboratoire de l'auteur pour analyse quant à la présence de drogues illégales. Sur base de l'explication de structure exécutée par la spectroscopie de résonance magnétique nucléaire et l'analyse du trimethylsilyl et les dérivés du trifluoroacétyle par la chromatographie en phaze gazeuse avec la spectrométrie de masse comme détection, il a été découvert que la poudre contenait de la drogue synthétique 4-methylamphétamine, en plus de l'amphétamine et de la caféine. Le spectre de masse d'impact électronique de 4-methylamphétamine obtenu par l'analyse d'une solution d'échantillon méthanolique a démontré un ion de base de m/z 56 plutôt que le m/z 44 attendu. Par conséquent, aucun résultat n'a été trouvé contenant un spectre de masse d'impact électronique présent dans la bibliothèque spectrale de masse et littérature. L'augmentation de 12 unités atomiques de masse a été expliquée par la formation d'adduit de formaldéhyde.

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Characterization of the synthesis of N,N‐dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry

Brandt

Moore

Freeman

et al. 2010

Drug Testing and Analysis

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The present study established an impurity profile of a synthetic route to the hallucinogenic N,N-dimethyltryptamine (DMT). The synthesis was carried out under reductive amination conditions between tryptamine and aqueous formaldehyde in the presence of acetic acid followed by reduction with sodium cyanoborohydride. Analytical characterization of this synthetic route was carried out by gas chromatography ion trap mass spectrometry using electron- and chemical-ionization modes. Methanol was employed as a liquid CI reagent and the impact of stoichiometric modifications on side-products formation was also investigated. Tryptamine 1, DMT 2, 2-methyltetrahydro-β-carboline (2-Me-THBC, 3), N-methyl-N-cyanomethyltryptamine (MCMT, 4), N-methyltryptamine (NMT, 5), 2-cyanomethyl-tetrahydro-β-carboline (2-CM-THBC, 6) and tetrahydro-β-carboline (THBC, 7) have been detected under a variety of conditions. Replacement of formaldehyde solution with paraformaldehyde resulted in incomplete conversion of the starting material whereas a similar replacement of sodium cyanoborohydride with sodium borohydride almost exclusively produced THBC instead of the expected DMT. Compounds 1 to 7 were quantified and the limits of detection were 28.4, 87.7, 21.5, 23.4, 41.1, 36.6, and 34.9 ng mL(-1), respectively. The limits of quantification for compounds 1 to 7 were 32.4, 88.3, 25.4, 24.6, 41.4, 39.9, and 37.0 µg mL(-1), respectively. Linearity was observed in the range of 20.8-980 µg mL(-1) with correlation coefficients > 0.99. The application holds great promise in the area of forensic chemistry where development of reliable analytical methods for the detection, identification, and quantification of DMT are crucial and also in pharmaceutical analysis where DMT might be prepared for use in human clinical studies.

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N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis

Cited by 9 publications

References 29 publications

Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis

Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis

Spectroscopic characterization of 4-methylamphetamine: formaldehyde adduct formation hindered the identification by mass spectrometry

Characterization of the synthesis of N,N‐dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry

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