title: An automated synthesis of N,N-dimethyl-2-(2-amino-4-[18F]fluorophenylthio)benzylamine (4-[18F]-ADAM) for imaging serotonin transporters.
abstract: N,N-dimethyl-2-(2-amino-4-[(18)F]fluorophenylthio)benzylamine (4-[(18)F]-ADAM, 3) is a potent serotonin transporter (SERT) imaging agent. In order to fulfill the demand of pre-clinical studies, we have developed an automated synthesis unit to synthesize this radioligand. The 4-[(18)F]-ADAM was synthesized using TracerLab FN and FE modules and a modified module control program (TracerLab-Fx). The synthesis sequences were similar to that of the manual synthesis, i.e. nucleophilic fluorination of N,N-dimethyl-2-(2,4-dinitrophenylthio)benzylamine (1) with K[(18)F]/K(2.2.2) followed by reduction with NaBH(4)/Cu(OAc)(2) and purifications with high-performance liquid chromatography (HPLC) and solid phase extraction. The radiochemical yield of 3 was 1.5+/-0.3% (n=13, EOS). The synthesis time was 120 min and the specific activity was 1.75+/-0.77 Ci/micromol (n=13, EOS). The 4-[(18)F]-ADAM synthesized by this module was stable over 4h at room temperature and is suitable for imaging SERT in humans.
authors.affiliation: Department of Nuclear Medicine, PET Center, Tri-Service General Hospital, 325 Section 2, Cheng-Kung Road, Neihu 114, Taipei, Taiwan.
authors.forename: Chi-Jiun
authors.initials: CJ
authors.lastname: Peng
authors.forename: Ya-Yao
authors.initials: YY
authors.lastname: Huang
authors.forename: Wen-Sheng
authors.initials: WS
authors.lastname: Huang
authors.forename: Chyng-Yann
authors.initials: CY
authors.lastname: Shiue
mesh_terms: D001331:Automation; D001596:Benzylamines / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D011786:Quality Control; D050486:Serotonin Plasma Membrane Transport Proteins / Q000032:analysis*
chemical_list: D001596:Benzylamines; C475911:N,N-dimethyl-2-(2-amino-4-fluorophenylthio)benzylamine; D050486:Serotonin Plasma Membrane Transport Proteins