The Analyst
January 1, 2005
Simon D. Brandt, Sally Freeman, Ian A. Fleet et al.
46 citations
The degree of alkylation of the side chain nitrogen in tryptamines influences psychoactivity. The Speeter and Anthony method, which reduces a substituted indole-3-yl-glyoxalylamide to the desired tryptamine with metal hydride, was used to synthesize 12 symmetrically and 13 asymmetrically N,N-disubstituted glyoxalylamides and their corresponding tryptamine derivatives. These compounds were characterized by gas chromatography EI-ion trap mass spectrometry, electrospray-triple quadrupole-tandem mass spectrometry, and NMR spectroscopy. A solvent dependency in NMR chemical shifts must be considered for unambiguous assignment. The 1H-NMR study allowed evaluation of rotamer populations of asymmetrical glyoxalylamides. For forensic or clinical monitoring, appropriate ion transitions focus on beta-cleavage and alpha-cleavage fragmentations. The analytical data aid in spectral identification of psychoactive tryptamines.
Drug Testing and Analysis
October 5, 2012
Simon Elliott, Simon D. Brandt, Sally Freeman et al.
36 citations
5-(2-Aminopropyl)indole (5-IT) and 3-(2-aminopropyl)indole (α-methyltryptamine, AMT) are isomeric substances that are difficult to differentiate under routine analytical conditions, especially without reference material. Subtle differences in mass spectral and UV conditions can facilitate their differentiation. Analyses included 1H and 13C NMR, GC-EI/CI ion trap MS, and several U/HPLC-DAD and HPLC-MS methods. AMT was detected in a number of fatal intoxications, and there is a potential risk of misidentification when dealing with both substances.
The Analyst
January 1, 2004
Simon D. Brandt, Sally Freeman, Ian A. Fleet et al.
27 citations
5-MeO-DIPT, a new psychoactive tryptamine derivative, was synthesized using the Speeter and Anthony procedure. The synthetic route was characterized by ESI-MS-MS, ESI-TOF-MS, and NMR. Side products were identified as 3-(2-N,N-diisopropylamino-ethyl)-1H-indol-5-ol, 2-N,N-diisopropylamino-1-(5-methoxy-1H-indol-3-yl)-ethanol, 2-(5-methoxy-1H-indol-3-yl)-ethanol, and 2-N,N-diisopropylamino-1-(5-methoxy-1H-indol-3-yl)-ethanone.
Drug Testing and Analysis
July 1, 2010
Simon D. Brandt, Sharon A. Moore, Sally Freeman et al.
14 citations
An impurity profile was established for a synthetic route to the hallucinogen N,N-dimethyltryptamine (DMT) using reductive amination of tryptamine with formaldehyde and reduction by sodium cyanoborohydride. Seven compounds were detected and quantified, including DMT and several byproducts. Replacing sodium cyanoborohydride with sodium borohydride almost exclusively produced tetrahydro-β-carboline instead of DMT. Detection limits ranged from 21.5 to 87.7 ng mL⁻¹, and quantification limits from 24.6 to 88.3 µg mL⁻¹, with linearity from 20.8 to 980 µg mL⁻¹. The method is useful for forensic and pharmaceutical analysis of DMT.
Journal of chromatography. A
August 14, 2009
Cláudia P.B. Martins, Sally Freeman, John F. Alder et al.
11 citations
A purported two-step internet recipe for making the psychoactive compound DMT was tested and found to produce almost none. The second step, methylation of tryptamine, was analyzed with advanced mass spectrometry. Instead of DMT, the reaction yielded 47.4% 1-N-methyl-TMT, 21.0% TMT, 11.1% unreacted tryptamine, and a 0.5% trace of N-methyltryptamine. The work demonstrates that synthetic methods circulated online can be unreliable and produce largely unintended, non-psychoactive products.
Forensic science international
July 4, 2008
Simon D Brandt, Cláudia P B Martins, Sally Freeman et al.
10 citations
DMT, a psychoactive compound, reacts with common laboratory solvents like dichloromethane (DCM) to form a quaternary ammonium salt, which can rearrange during analysis into products including 3-(2-chloroethyl)indole and 2-methyltetrahydro-beta-carboline. This study extends these findings to other halogenated solvents—dibromomethane and 1,2-dichloroethane—characterizing the resulting derivatives. The DCE derivative produced at least six rearrangement products. Using deuterated compounds helped clarify the rearrangement mechanisms. These solvent-derived marker molecules could help identify which solvents were used in the manufacture of controlled substances, a factor often overlooked because solvents are assumed inert.
Journal of Pharmaceutical and Biomedical Analysis
December 28, 2007
Simon D. Brandt, Cláudia P.B. Martins, Sally Freeman et al.
10 citations
DMT, a simple tryptamine with powerful psychoactive properties, reacts with dichloromethane during work-up or long-term storage, forming the quaternary ammonium salt N-chloromethyl-DMT chloride. Analysis of this side-product by gas chromatography ion trap mass spectrometry (GC-MS) yielded only degradation products, such as 3-(2-chloroethyl)indole and 2-methyltetrahydro-beta-carboline, while HPLC detected the original salt. Because GC-MS is standard for drug fingerprinting, the presence of these degradation products could lead to erroneous conclusions about the synthetic route of a DMT sample.
The Analyst
January 1, 2005
Simon D. Brandt, Sally Freeman, Ian A. Fleet et al.
10 citations
Twelve symmetrically and 13 asymmetrically N,N-disubstituted glyoxalylamide precursors and their corresponding tryptamine derivatives were characterized using gas chromatography low-pressure chemical ionization ion trap tandem mass spectrometry with methanol as the chemical ionization reagent. In tryptamines, formation of [CH2=N+R2R3] iminium ions after beta-cleavage dominates, while dissociation into [3-vinylindole]+ is a minor pathway compared to electrospray triple quadrupole tandem mass spectrometry, where that transition is distinctively important. This method also enables differentiation between most isomeric derivatives studied.