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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Brain / diagnostic imaging
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Brain / metabolism*
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Carrier Proteins / analysis
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Carrier Proteins / metabolism*
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Cocaine / analogs & derivatives*
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Cocaine / chemical synthesis
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Cocaine / pharmacokinetics
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Dopamine / metabolism
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Dopamine Plasma Membrane Transport Proteins
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Fluorine Radioisotopes / pharmacokinetics*
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Humans
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Membrane Glycoproteins*
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Membrane Transport Proteins*
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Molecular Conformation
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Molecular Structure
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Nerve Tissue Proteins*
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Tomography, Emission-Computed / methods
Substances
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3beta-(2-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester
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3beta-(4-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester
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Carrier Proteins
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Dopamine Plasma Membrane Transport Proteins
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Fluorine Radioisotopes
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Membrane Glycoproteins
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Membrane Transport Proteins
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Nerve Tissue Proteins
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Cocaine
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Dopamine