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• W2121662506 abstract "N-Alkylated tryptamines have complex psychoactive properties. Routes for clandestine synthesis are described on Internet websites one of which involves the thermolytic decarboxylation of tryptophan to tryptamine as a precursor to psychoactive compounds. High boiling solvents and ketone catalysts have been employed to facilitate the decarboxylation of tryptophan. The present study has revealed that there is formation of tetrahydro-beta-carboline (THBC) derivatives which may originate from reaction with both the solvent and the ketone catalyst. The application of gas chromatography electron- and chemical-ionisation ion trap tandem mass spectrometry (GC-IT-MS-MS), in combination with nuclear magnetic resonance (NMR), led to the isolation and identification of 1,1-disubstituted-tetrahydro-beta-carbolines formed as major impurities in the tryptamine. Confirmation was by synthesis of the THBC derivatives from tryptamine using Pictet-Spengler cyclisation. Under EI-conditions, mass spectral characterisation of the THBCs suggests predominance of alkyl cleavage. These impurities will yield a useful profile for identification of the synthetic pathway and likely reagents employed, particularly a fingerprint of the ketone catalyst and an insight into the influence of solvents and catalysts on the formation of by-products." @default.
• W2121662506 created "2016-06-24" @default.
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• W2121662506 date "2006-06-01" @default.
• W2121662506 modified "2023-09-27" @default.
• W2121662506 title "Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-β-carboline formation" @default.
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• W2121662506 doi "https://doi.org/10.1016/j.jpba.2006.02.007" @default.
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