Microbial transformation of 3,4-methylenedioxy-N-methylamphetamine and 3,4-methylenedioxyamphetamine

Abstract

The biotransformation of 3,4-methylenedioxy-N-methylarnphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) was examined in the fungus Cunninghamella echinulata. In addition to the reported mammalian metabolites (MDA, 3,4-methylenedioxybenzyl methyl ketoxime, 3,4-methylenedioxybenzyl methyl ketone) and the parent substrate, there were six novel metabolites detected. N-Acetyl-3,4-methylenedioxyamphetamine (NAcMDA) was unequivocally identified and three unidentified metabolites related to NAcMDA were also detected. N-Acetyl-3,4-methylenedioxy-1-phenyl-1-hydroxy-2-aminopropane was tentatively identified as a metabolite of MDMA. The only metabolite of MDA identified was NAcMDA. Two metabolites related to MDA remain unidentified.Key words: Cunninghamella, amphetamine, biotransformation, 3,4-methylenedioxy-N-methylamphetamine, 3,4-methylenedioxyamphetamine.