title: Synthesis of 3beta-(4-[18F]fluoromethylphenyl)- and 3beta-(2-[18F] fluoromethylphenyl)tropane-2beta-carboxylic acid methyl esters: new ligands for mapping brain dopamine transporter with positron emission tomography.
abstract: The synthesis of two new dopamine transporter ligands, 3beta-(4-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester and 3beta-(2-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester, and their spectral characterization are described. The precursors for these ligands were prepared by TiCl4 catalyzed chloromethylation of 3beta-phenyltropane-2beta-carboxylic acid methyl ester followed by separation of the isomeric product mixture of 2- and 4-chloromethylphenyltropane derivatives. Reaction of the chloromethyl analogs with no-carrier-added [18F]fluoride ion followed by high performance liquid chromatography purification provided the corresponding [18F]fluoromethyltropanes, in good radiochemical yields, useful for imaging the brain dopamine transporter system in vivo with positron emission tomography.
authors.affiliation: Department of Molecular and Medical Pharmacology, UCLA School of Medicine, Los Angeles, California 90095-6948, USA. p6
authors.forename: A
authors.initials: A
authors.lastname: Petric
authors.forename: J R
authors.initials: JR
authors.lastname: Barrio
authors.forename: M
authors.initials: M
authors.lastname: Namavari
authors.forename: S C
authors.initials: SC
authors.lastname: Huang
authors.forename: N
authors.initials: N
authors.lastname: Satyamurthy
mesh_terms: D001921:Brain / Q000000981:diagnostic imaging / Q000378:metabolism*; D002352:Carrier Proteins / Q000032:analysis / Q000378:metabolism*; D003042:Cocaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics; D004298:Dopamine / Q000378:metabolism; D050483:Dopamine Plasma Membrane Transport Proteins; D005462:Fluorine Radioisotopes / Q000493:pharmacokinetics*; D006801:Humans; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D008968:Molecular Conformation; D015394:Molecular Structure; D009419:Nerve Tissue Proteins; D014055:Tomography, Emission-Computed / Q000379:methods
chemical_list: C400122:3beta-(2-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester; C400123:3beta-(4-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester; D002352:Carrier Proteins; D050483:Dopamine Plasma Membrane Transport Proteins; D005462:Fluorine Radioisotopes; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D003042:Cocaine; D004298:Dopamine