Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives.
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.
Trachsel
Daniel
D
daniel_trachsel@gmx.ch
Hadorn
Marcel
M
Baumberger
Franz
F
D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005459:Fluorides / Q000138:chemical synthesis*
D015104:3,4-Methylenedioxyamphetamine; D005459:Fluorides