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Synthesis of Fluoro Analogues of 3,4‐(Methylenedioxy)amphetamine (MDA) and Its Derivatives
Author(s) -
Trachsel Daniel,
Hadorn Marcel,
Baumberger Franz
Publication year - 2006
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200690035
Subject(s) - methylenedioxy , mdma , chemistry , neurotoxicity , amphetamine , methamphetamine , steric effects , pharmacology , stereochemistry , toxicity , psychology , neuroscience , alkoxy group , organic chemistry , medicine , dopamine , alkyl
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.