Crystal Structure of a Fluoro Analogue of 3,4-(Methylenedioxy)amphetamine
J. Guillon, N. Pinaud, M. Marchivie, L. Ronga, A. Benazzouz, S. Moreau
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper |
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| Key points | Reports the structural characterization, including the crystal structure, of 6-fluoro-3,4-methylenedioxyamphetamine, a newly prepared fluoro analogue of 3,4-(methylenedioxy)amphetamine. The authors argue that despite being electronically different, the fluoro analogues should be sterically very similar to the non-fluorinated parent compounds, supporting their use in investigating MDMA metabolism and in synthesizing [18F]fluoroamphetamines for PET studies. |
Abstract
Parkinson’s disease is due to a dopamine deficiency caused by the degeneration of midbrain dopamine neurons. Current therapies are aimed to substitute dopamine or to directly stimulate postsynaptic dopamine receptors. However, not all patients profit from current therapies to the same extent, even serious side effects such as dyskinesias are complicating the therapy.1 It has been suggested that methylenedioxy analogues of amphetamine (i.e. 3,4-methylenedioxyamphetamine (MDA), MDMA, 3,4-methylenedioxyethylamphetamine (MDE), N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB)) could represent a novel class of drugs. Thus, MDMA has recently been identified as a potential therapeutic drug against Parkinson’s disease in animals.2 Furthermore, MDMA may also help to treat people with posttraumatic-stress disorder.2 Consequently, new fluoro analogues of 3,4-(methylenedioxy)amphetamine could be developed and investigated for PET studies in order to further synthesize [18F]fluoroamphetamines.3 Thus, to prompt investigation into the role of MDMA metabolism, new fluoro analogues of 3,4-(methylenedioxy)amphetamine were prepared and characterized. Although electronically very different, the fluoro analogues should be sterically very similar to the non-fluorinated parent compounds. We report herein on the structural characterization of one of them, i.e. the 6-fluoro-3,4-methylenedioxyamphetamine Crystal Structure of a Fluoro Analogue of 3,4-(Methylenedioxy)amphetamine