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Synthesis of racemic, S(+)‐ and R(‐)‐N‐[methyl‐ 3 H]3,4‐methylenedioxymethamphetamine
Author(s) -
Hashimoto Kenji,
Hirai Katsumi,
Goromaru Tsuyoshi
Publication year - 1990
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580280415
Subject(s) - chemistry , methyl iodide , high performance liquid chromatography , tritium , chromatography , desmethyl , yield (engineering) , iodide , alkylation , radiochemistry , medicinal chemistry , organic chemistry , metabolite , catalysis , biochemistry , physics , materials science , nuclear physics , metallurgy
The synthesis of 3,4‐methylenedioxymethamphetamine(MDMA), a serotonergic neurotoxin, labeled with tritium is described. Labeling was accomplished by N‐alkylation of the free base of the corresponding desmethyl compound using [ 3 H]methyl iodide. The compound was purified by preparative HPLC. The radiochemical yield was about 60% based on [ 3 H]methyl iodide. The radiochemical purity was more than 95% from HPLC and TLC. Furthermore, S(+)‐ and R(‐)‐[ 3 H]MDMA were completely separated by analytical HPLC with chiral column.
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