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Chem Biodivers. 2006 Mar;3(3):326-36.

Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives.

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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.

[Indexed for MEDLINE]

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