Author Topic: MDMA/MADAM-6 Synthesis/Biodistribution  (Read 1836 times)

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MDMA/MADAM-6 Synthesis/Biodistribution
« on: April 21, 2004, 08:37:00 AM »
N-[11C]methyl-3,4-methylenedioxyamphetamine (Ecstasy) and 2-methyl-N-[11C]methyl-4,5-methylenedioxyamphetamine: Synthesis and biodistribution studies
M. Patt, D. Gündisch, U. Wüllner, A. Blocher, K.-A. Kovar, H.-J. Machulla

Journal of Radioanalytical and Nuclear Chemistry 240(2), 535–540 (1999)


In order to evaluate the neurobiological mechanism causing the psychogenic effects of methylenedioxy-derivatives of amphetamine, the carbon-11 labeled analogues of 3,4-methylenedioxymethamphetamine (MDMA), 2 and 2,N-dimethyl-4,5-methylenedioxyamphetamine (MADAM-6) 4 were prepared for application in in-vivo PET studies by methylation of 3,4-methylenedioxyamphetamine (MDA) 1 and 2-methyl-4,5-methylenedioxyamphetamine 3 with [11C]CH3I. The radiochemical yield was determined in dependence on time, temperature. and amount of precursor. The best conditions for a fast labeling reaction with carbon-11 on a preparative scale were found to be a reaction time of 10 min using 1 mg of the corresponding dimethyl-precursors 1 or 3, thus obtaining radiochemical yields of 60% (based on produced [11C]CH3I) Biodistribution studies were performed in rats, a high brain to blood ratio of 7.5 was observed for [11C]MDMA in contrast to a ratio of 3.7 for [11C]MADAM-6.