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Synthesis of Fluoro Analogues of 3,4-(Methylenedioxy)amphetamine (MDA) and Its Derivatives

✍ Scribed by Daniel Trachsel; Marcel Hadorn; Franz Baumberger

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
103 KB
Volume
3
Category
Article
ISSN
1612-1872

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✦ Synopsis

Abstract

The role of the metabolism of the entactogen 3,4‐(methylenedioxy)methamphetamine (MDMA; 1b) in neurotoxic or psychopharmacologic action is widely discussed, but not yet fully understood. To prompt further investigation into the role of MDMA metabolism, six new 3,4‐(difluoromethylenedioxy) analogues of MDMA (1b) were prepared and characterized. Although electronically very different, the fluoro analogues 3–5 should be sterically very similar to the non‐fluorinated parent compounds. The F‐atoms may prevent the formation of toxic metabolites produced via a radical pathway (Scheme 1). Different theories regarding MDMA‐induced neurotoxicity are briefly reviewed and discussed. The novel compounds 3–5 may help to verify the hypothesis that MDMA‐induced neurotoxicity is the result of the formation of metabolites lacking the methylenedioxy bridge.

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