PT - JOURNAL ARTICLE AU - Mun, Jiyoung AU - Murnane, Kevin AU - Howell, Leonard AU - Goodman, Mark TI - S(+)-, and R(-)-3,4-methylenedioxy-N-[<sup>11</sup>C]methamphetamine (MDMA, Ecstasy) were synthesized and stereochemistry was confirmed to compare pharmacokinetics of each enantiomer using positron emission tomography DP - 2012 May 01 TA - Journal of Nuclear Medicine PG - 1616--1616 VI - 53 IP - supplement 1 4099 - http://jnm.snmjournals.org/content/53/supplement_1/1616.short 4100 - http://jnm.snmjournals.org/content/53/supplement_1/1616.full SO - J Nucl Med2012 May 01; 53 AB - 1616 Objectives 3,4-Methylenedioxymethamphetamine (MDMA), also known as“ecstasy”, is a drug with high abuse liability that represents a significant public health concern. Previous studies have indicated that the psychobiology of S(+)-MDMA is stimulant-like, whereas that of R(-)-MDMA is hallucinogen-like. Each enantiomer was labeled with carbon-11 as 3,4-methylenedioxy-N-[11C]methamphetamine, and stereochemistry was confirmed by chiral HPLC, to measure pharmacokinetics with positron emission tomography. Methods S(+)-, and R(-)-MDA•HCl were neutralized and purified as free amines. 1.7 - 2.1mg of MDA was dissolved in 170 - 210µL of DMF with a concentration of 1mg/100µL and mixed with [11C]methyl iodide produced by GE TRACERlab FX C. The reaction mixture was heated at 140oC for 10 minutes, [11C]MDMA was purified by HPLC, and formulated in 15mL of physiological saline containing 10% of ethanol. The quality control was performed by HPLC coupled with a UV and a radiometric detector. The stereochemistry of each enantiomeric [11C]MDMA was confirmed by Astec chirobiotic TAGTM chiral HPLC. Data were obtained as an average of nine syntheses. Results Decay corrected yield was 40% based on [11C]methyl iodide activity, reaction time was 56 minutes from end of bombardment , specific activity at end of synthesis was 7.03GBq/µmole (0.19Ci/µmole) at end of synthesis, radiochemical purity was over 97%, and pH of a dose solution was 7. Figure 1 presents the stereochemistry and TAC curves of each enantiomeric [11C]MDMA injected into non-human primates. Conclusions S(+)-, and R(-)-[11C]MDMA was synthesized with quality and reproducibility for pharmacokinetics studies in non-human primates