Synthesis of racemic, S(+)‐ and R(‐)‐N‐[methyl‐3H]3,4‐methylenedioxymethamphetamine
Kenji Hashimoto, Katsumi Hirai, Tsuyoshi Goromaru
Journal of Labelled Compounds and Radiopharmaceuticals April 1, 1990 DOI: 10.1002/jlcr.2580280415 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | MDMA |
| Key points | The authors report a synthesis of tritium-labeled MDMA via N-alkylation of the desmethyl free base with [3H]methyl iodide, giving about 60% radiochemical yield and over 95% radiochemical purity, with complete separation of the S(+) and R(-) enantiomers by chiral analytical HPLC. |
Abstract
AbstractThe 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 [3H]methyl iodide. The compound was purified by preparative HPLC. The radiochemical yield was about 60% based on [3H]methyl iodide. The radiochemical purity was more than 95% from HPLC and TLC. Furthermore, S(+)‐ and R(‐)‐[3H]MDMA were completely separated by analytical HPLC with chiral column.
Citations in the library
Cited by 3
- Synthesis of R- and S-MDMA via nucleophilic ring-opening of homochiral N-tosylaziridines Australian Journal of Chemistry July 11, 2023
- Drug effects on distribution of [3H]3,4-methylenedioxymethamphetamine in mice. European Journal of Pharmacology April 1, 1993
- Reduction of in vivo binding of [3H]paroxetine in mouse brain by 3,4-methylenedioxymethamphetamine. Neuropharmacology July 1990
Cites 5
- Neurotoxicity of the psychedelic amphetamine, methylenedioxymethamphetamine. Journal of Pharmacology and Experimental Therapeutics 1987
- 3,4-Methylenedioxymethamphetamine and 3,4-methylenedioxyamphetamine destroy serotonin terminals in rat brain: quantification of neurodegeneration by measurement of [3H]paroxetine-labeled serotonin uptake sites. Journal of Pharmacology and Experimental Therapeutics September 1, 1987
- The Background and Chemistry of MDMA Journal of Psychoactive Drugs October 1, 1986
- Effects of 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethamphetamine isomers on central serotonergic, dopaminergic and nigral neurotensin systems of the rat. Journal of Pharmacology and Experimental Therapeutics March 1, 1988
- Immediate and long-term effects of 3,4-methylenedioxymethamphetamine on serotonin pathways in brain of rat. Neuropharmacology December 1987