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

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

doi:10.1016/j.forsciint.2008.03.013

Cited by 10 publications

(17 citation statements)

References 22 publications

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“…R1 R2 R3 Name (Table 1). 36 When this was compared with shortened reaction times of 5, 10, and 15 min, it was interesting to observe that comparable yields and product purities were obtained (HPLC analysis, data not shown). These findings led to the application of a 5 min reduction to the preparation of 22 N,N-dialkylated a,a,b,b-d 4 -tryptamines (Table 1) with good yields.…”

Section: Resultsmentioning

confidence: 97%

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d₄]‐tryptamines

Brandt

Tirunarayanapuram

Freeman

et al. 2008

Labelled Comp Radiopharmac

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A large number of N,N-dialkylated tryptamines are known to induce psychoactive effects in humans. This has resulted in their increased attention within clinical and forensic communities. Deuterated tryptamines are ideal for use as internal standards during MS bioanalysis or of use in biochemical NMR studies. The present study reports on a microwave-enhanced synthesis of 22 N,N-dialkylated-[a,a,b,b-d4]-tryptamines via the reduction with lithium aluminium deuteride of glyoxalylamide precursors obtained by the procedure of Speeter and Anthony. Syntheses were carried out using a single-mode system under elevated pressure conditions where anhydrous tetrahydrofuran was used as the solvent at 1501C. Good yields were obtained within 5 min.

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Section: Resultsmentioning

confidence: 97%

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d₄]‐tryptamines

Brandt

Tirunarayanapuram

Freeman

et al. 2008

Labelled Comp Radiopharmac

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“…Almost none of these studies reported analyte recoveries, however. Another potential problem, involving co-injection of extracted indoleethylamines in GC analyses using the solvent methylene chloride, was addressed by Brandt et al [86] These authors showed that the compounds of interest react with methylene chloride under such conditions, forming quaternary salts and analytical artifacts. [67][68][69] In addition to methodological complications, misidentifications of compounds may also have occurred because both paper and TLC using colour reagents require a somewhat subjective interpretation.…”

Section: Mdmt: Urinementioning

confidence: 99%

“…For example, Rodnight [2] and Siegel et al [12] proposed that the substance detected by Bumpus and Paige [1] was tryptamine and not HDMT. Another potential problem, involving co-injection of extracted indoleethylamines in GC analyses using the solvent methylene chloride, was addressed by Brandt et al [86] These authors showed that the compounds of interest react with methylene chloride under such conditions, forming quaternary salts and analytical artifacts.…”

Section: Mdmt: Urinementioning

confidence: 99%

“…For example, are DMT, HDMT, and/or MDMT truly present in humans? [86] Biological factors that may have affected the detectabilty of these compounds in the periphery were also acknowledged, which included their rapid metabolism. [2,12] Further, it was claimed that possible artifacts produced from the extraction solvents and conditions of analysis may have led to misidentification of the DMTs in some early studies [20] and, more recently, that the use of halogenated solvents in the analysis may have affected their detection.…”

Section: Introductionmentioning

confidence: 99%

“…[2,12] Further, it was claimed that possible artifacts produced from the extraction solvents and conditions of analysis may have led to misidentification of the DMTs in some early studies [20] and, more recently, that the use of halogenated solvents in the analysis may have affected their detection. [86] Biological factors that may have affected the detectabilty of these compounds in the periphery were also acknowledged, which included their rapid metabolism. [87,88] Finally, there have been concerns that the studies searching for their presence and an association with specific clinical disorders have failed to understand and fully characterize their metabolism or monitor their metabolites.…”

Section: Introductionmentioning

confidence: 99%

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A critical review of reports of endogenous psychedelic N, N‐dimethyltryptamines in humans: 1955–2010

Barker

McIlhenny

Strassman

2012

Drug Testing and Analysis

105

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Three indole alkaloids that possess differing degrees of psychotropic/psychedelic activity have been reported as endogenous substances in humans; N,N‐dimethyltryptamine (DMT), 5‐hydroxy‐DMT (bufotenine, HDMT), and 5‐methoxy‐DMT (MDMT). We have undertaken a critical review of 69 published studies reporting the detection or detection and quantitation of these compounds in human body fluids. In reviewing this literature, we address the methods applied and the criteria used in the determination of the presence of DMT, MDMT, and HDMT. The review provides a historical perspective of the research conducted from 1955 to 2010, summarizing the findings for the individual compounds in blood, urine, and/or cerebrospinal fluid. A critique of the data is offered that addresses the strengths and weaknesses of the methods and approaches to date. The review also discusses the shortcomings of the existing data in light of more recent findings and how these may be overcome. Suggestions for the future directions of endogenous psychedelics research are offered. Copyright © 2012 John Wiley & Sons, Ltd.

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

Cited by 10 publications

References 22 publications

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d₄]‐tryptamines

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d₄]‐tryptamines

A critical review of reports of endogenous psychedelic N, N‐dimethyltryptamines in humans: 1955–2010

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

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

Cited by 10 publications

References 22 publications

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d4]‐tryptamines

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d4]‐tryptamines

A critical review of reports of endogenous psychedelic N, N‐dimethyltryptamines in humans: 1955–2010

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

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Product

Resources

About

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d₄]‐tryptamines

Microwave‐accelerated synthesis of psychoactive deuterated N,N‐dialkylated‐[α,α,β,β‐d₄]‐tryptamines