Comparison of the Characteristic Mass Fragmentations of Phenethylamines and Tryptamines by Electron Ionization Gas Chromatography Mass Spectrometry, Electrospray and Matrix-Assisted Laser Desorption Ionization Mass Spectrometry

Abstract

Characteristic mass fragmentation of 20 phenethylamine/tryptamine standards were investigated and compared by means of matrix assisted laser desorption/time-of-flight mass spectrometry (MALDI/TOFM), gas chromatography-electron ionization-mass spectrometry (GC-EI/MS) and liquid chromatography-electrospray ionization/mass spectrometry (LC-ESI/MS) methods. As a result, three characteristic peaks ([M] + and fragments from the C β-C α bond breakage) were found to be unique and contained information useful in identifying 2C series compounds based on the GC-EI/MS method. We found that the protonated molecular ion ([M+H] +) and two types of fragments produced from the α-cleavage and β-cleavage processes were useful mass spectral information in the rapid screening and confirmation of phenethylamine and tryptamine derivatives when ESI/MS and MALDI/TOFMS methods were applied. This assay was successfully used to determine samples that contain illicit drugs.

Mechanistic understanding of microstructure formation during synthesis of metal oxide/carbon nanocomposites

“…The peaks in the prole of m/z = 30 can be assigned to the base peak ion [CH 2 NH 2 ] + , characteristic of bcleavage of OA molecule. 45,46 Finally, the signal at m/z = 28 can be attributed to hydrocarbons, CO 2 , or N 2 , and m/z = 44 can be attributed to hydrocarbons (C 3 H 8 ) or CO 2 . 44 FTIR results in Fig.…”

Spectral trends in GC-EI-MS data obtained from the SWGDRUG mass spectral library and literature: A resource for the identification of unknown compounds

“…Phenethylamines are another class of compounds increasingly being observed in casework that, like synthetic cannabinoids, have a wide range of core structures. These core structures include amphetamine-like, "2C"-series, "D"-series, "NBOMe"-series, "FLY"series, and "DRAGONFLY"-series compounds [114][115][116][117][118]. These molecules sub-groups are based on the different substitutions found on the aromatic ring (R1), on the α and β-carbon alkyl chain (Rα and Rβ), or on the nitrogen atom (RN) (Figure 12).…”

Interpol review of controlled substances 2016–2019

“…Amphetamine-Type Stimulants (ATSs) and Related Phenethylamines (PEAs): 2016 A solid colorimetric sensor for the analysis of amphetamine-like street samples with a LOD of 0.002–0.005 g mL(-1) [ 863 ]; differential mobility spectrometry (DMS-MS/MS) analysis of nine structurally similar amphetamine-type stimulants compared to LC-MS/MS [ 864 ]; 22 amphetamine-derived synthetic drugs, mostly cathinones, were examined by GC-MS using two different derivatization methods (i) heptafluorobutyric anhydride (HFBA) and (ii) pentafluorobenzoyl chloride (PFBCl) [ 865 ]; 2017 statistical comparison of mass spectra for identification of amphetamine-type stimulants [ 866 ]; Indirect chiral separation of 8 novel amphetamine derivatives as potential new psychoactive compounds by GC-MS and HPLC [ 867 ] ; Destruction of ATS in aqueous solution using gamma irradiation [ 868 ]; point-of-use detection of ATS with host-molecule-functionalized organic transistors (sensor) [ 869 ]; Statistical comparison of mass spectra for identification of amphetamine-type stimulants including amphetamine, methamphetamine, MDA, MDMA, phentermine, and psilocin [ 870 ]; chromatographic differentiation of the ring-substituted regioisomers of amphetamine and methamphetamine by supercritical fluid chromatography [ 871 ]; Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe, seized from clandestine laboratories and analyzed by LC-QTOF-MS, GC-MS and NMR [ 872 ]; analysis of synthetic phenethylamine street drugs using direct sample analysis coupled to accurate mass TOF-MS [ 873 ]; wearable sensor device for the rapid and sensitive detection of amphetamine-type stimulants [ 874 ]; quantum chemical investigation of neutral and cationic phenylethylamine, amphetamine and methamphetamine [ 875 ]; enantioresolution of 12 drugs (including phenethylamines) by CE [ 876 ]; investigation of characteristic mass fragmentation of 20 phenethylamine/tryptamine standards by MALDI/TOFM, GC-EI/MS and LC-ESI/MS [ 877 ]; LC-QTOF-MS, GC-MS and NMR for identification of phenethylamine derivatives seized from a clandestine laboratory, including 5-(2-methylaminopropyl)-2,3-dihydrobenzofuran (5-MAPDB, 1), 5-(2-aminoethyl)-2,3-dihydrobenzofuran (5-AEDB, 2), N,2-dimethyl-3-(3,4-methylenedioxyphenyl)propan-1-amine (MDMA methylene homolog, 3), 6-bromo-3,4-methylenedioxymethamphetamine (6-Br-MDMA, 4), and 1-(benzofuran-5-yl)-N-(2-methoxybenzyl)propan-2-amine (5-APB-NBOMe, 5) [ 872 ]; 2018 SUPRAS extraction approach for matrix-independent determination of amphetamine-type stimulants by LC-MS/MS [ 878 ]; use of CE coupled to TOF-MS for simultaneous chiral separation of amphetamine-type stimulants and ephedrine for the identification of chiral characteristics of methamphetamine seizures in Shanghai for inferring the synthetic pathways of drugs [ 879 ]; detection of t-Boc-methamphetamine (t-Boc-MP) by DART-TOF-MS and evaluation of the method in comparison with GC-MS and LC-TOF-MS [ ...…”

“…Tryptamines (see also Mushrooms): 2016 square wave adsorptive stripping voltammetry for determination of tryptamine [ 1181 ]; synthesis of synthesis of 3-(2-(1H-indol-3-yl)ethyl)-4-hydroxy-4-arylthiazolidine-2-thione and 3-(2-(1H-indol-3-yl)ethyl)-4-arylthiazole-2(3H)-thione [ 1182 ]; synthesis of functionalized 3-{1-[2-(1H-indol-3-yl) ethyl]-4,5,6,7-tetra-hydro-1H-indol-3-yl} indolin-2-ones [ 1183 ]; HPLC-DAD method for detecting terpenoid indole alkaloids in different parts and different developmental stages of Catharanthus roseus plants [ 1184 ]; Solid Surface-Room Temperature Phosphorescence (SS-RTP) for direct determination of the concentration of tryptamine in beers [ 1185 ]; RP-HPLC-DAD for determination of the biogenic amines tryptamine, putrescine, histamine, phenylethylamine, tyramine, cadaverine, spermidine and spermine in red and white wines [ 1186 ]; 2017 analytical characterization of 17 DALTs using NMR, GC quadrupole and ion trap (EI/CI) MS, low and high mass accuracy MS/MS, photodiode array detection, and GC solid-state infrared analysis [ 1187 ]; LC-MS method for quantification of Tryptophan [ 1188 ]; characterization of omega-N-methyl-4-hydroxytrypt-amine (norpsilocin, 1) using 1D and 2D NMR spectroscopy and high-resolution mass spectrometry [ 789 ]; detection of 5-fluoro-DALT (5-F-DALT), 7-methyl-DALT (7-Me-DALT), and 5,6-methylenedioxy-DALT (5,6-MD-DALT) using GC-MS, LC-MS/MS and LC-HR-MS/MS [ 1189 ]; GC-MS analysis of 25,296 samples of which 436 were tryptamines; from these 232 (53.21%) were non-regulated (the most delivered non-regulated tryptamine was 4-AcO-DMT) [ 1190 ]; SPE-LC-UV-DAD for determination of tryptamines Ayahuasca, a potent hallucinogenic beverage [ 552 ]; use of tryptamine as a reactive matrix for the analysis of non-polar carbonyl compounds by MALDI-MS [ 1191 ]; UPLC-TQ/MS method for direct determination of biogenic amines tryptamine, putrescine, histamine, phenylethylamine, tyramine, cadaverine, spermine, and spermidine in wine [ 1192 ]; 2018 detection of 5-MeO-2-Me-DALT, 5-MeO-2-Me-ALCHT, 5-MeO-2-Me-DIPT using GC-MS, LC-MSn and LC-HR-MS/MS [ 1193 ]; investigation and comparison of mass fragmentation of 20 phenethylamine/tryptamine standards by means of MALDI/TOFM, GC-EI/MS and LC-ESI/MS [ 877 ]; trends in use of tryptamines-specifically DMT, alpha-methyltryptamine (AMT), and 5-MeO-DIPT (“Foxy”) [ 1194 ];…”