Journal of Labelled Compounds and Radiopharmaceuticals
August 14, 2006
Ya-Zhu Xu, Chinpiao Chen
14 citations
A deuterium-labeled version of the psychedelic compound N,N-dimethyltryptamine (DMT) was synthesized. Starting from a commercially available nitroaromatic compound, the 5-methoxy group was labeled with three deuterium atoms using deuterated iodomethane. The synthesis followed the Batcho-Leimgruber indole synthesis, then introduced the side chain via oxalyl chloride and dimethylamine, and finally reduced the amide with lithium aluminum hydride to give 5-[2H3]-methoxy-N,N-dimethyltryptamine.
Journal of Labelled Compounds and Radiopharmaceuticals
June 1, 2007
Ajam C. Shaikh, Yu‐yun Wang, Chinpiao Chen
9 citations
A method for synthesizing deuterium-labeled versions of two psychoactive amphetamine derivatives, DOM and MMDA, is described. The labeled compounds are intended for use as internal standards in gas chromatography–mass spectrometry (GC–MS) assays to improve measurement accuracy.
Journal of Labelled Compounds and Radiopharmaceuticals
April 1, 1994
Herbert H. Seltzman, Denise F. Odear, Christopher P. Laudeman et al.
7 citations
A new method introduces tritium into aryl compounds using tritium gas directly on the underivatized substrate. By combining directed ortho metallation with a reduction of the carbon-potassium bond, tritium is incorporated at high specific activity under mild conditions. The approach is demonstrated by preparing tritium-labeled ibogaine, showing its utility for synthesizing radiolabeled compounds for research.
Journal of Labelled Compounds and Radiopharmaceuticals
October 1, 2007
Yu Yun Wang, Chinpiao Chen
6 citations
A synthetic route to deuterium-labeled bufotenine (5-HO-DMT) was developed using the Batcho–Leimgruber strategy. Starting from commercial 3-methyl-4-nitrophenol, the synthesis proceeded through benzyl protection and reaction with N,N-dimethylformamide–dimethylacetal. Reduction with Raney nickel and hydrazine hydrate gave an indole intermediate, which was then treated with oxalyl chloride, dimethylamine, and lithium aluminum [2H4]-hydride to introduce four deuterium atoms. Final hydrogenolysis removed the benzyl ether, yielding the labeled bufotenine. This method enables the preparation of a deuterated analog of the psychoactive compound for use in tracer studies or metabolic investigations.
Journal of Labelled Compounds and Radiopharmaceuticals
July 1, 2025
Rodney D. Brown, Niall M. Hamilton, Connor Mallon et al.
1 citation
Three new radiolabelled versions of the psychedelic compounds psilocin, psilocybin, and 5-MeO-DMT were synthesized, each with carbon-14 at the 2-position of the indole ring. The synthesis used a common route: attaching the dimethylaminoethyl side chain to substituted indole intermediates via oxalyl chloride, dimethylamine, and lithium aluminium hydride reduction. Psilocybin-2-14C at 234 μCi/mg showed limited stability, but a 5.5-fold dilution with unlabelled psilocybin maintained >97.5% radiochemical purity after one month at ≤−70°C. 5-MeO-DMT-2-14C succinate at 173 μCi/mg remained 98.0% pure after six months at ≤−70°C, supporting long-term studies. These labelled compounds enable in vivo pharmacokinetic and metabolic studies of psychedelic tryptamines, aiding ADME and mass balance research for potential regulatory approval in treating depression, anxiety, and PTSD.