Synthesis of [ O-methyl- 11C]fluvoxamine—a potential serotonin uptake site radioligand

5-Methoxy-1-[4-(trifluoromethyl)-phenyl]-1-pentanone- O-(2-aminoethyl)oxime (fluvoxamine), a potent clinically used antidepressant, was labelled with carbon-11 ( t 1 2 = 20.4 min ) as a potential radioligand for the non-invasive assessment of serotonin uptake sites in the human brain with positron e...

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Bibliographic Details
Published in:Applied radiation and isotopes 1997-06, Vol.48 (6), p.749-754
Main Authors: Matarrese, M., Soloviev, D., Todde, S., Magni, F., Colombo, D., Kienle, M.Galli, Fazio, F.
Format: Article
Language:English
Subjects:
Binding Sites
Brain - metabolism
Carbon Radioisotopes
Fluvoxamine - analogs & derivatives
Fluvoxamine - chemical synthesis
Fluvoxamine - metabolism
Fluvoxamine - pharmacology
Humans
Methods
Methylation
Radioligand Assay
Serotonin - metabolism
Serotonin Uptake Inhibitors - chemical synthesis
Serotonin Uptake Inhibitors - metabolism
Serotonin Uptake Inhibitors - pharmacology
Tomography, Emission-Computed
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Summary:5-Methoxy-1-[4-(trifluoromethyl)-phenyl]-1-pentanone- O-(2-aminoethyl)oxime (fluvoxamine), a potent clinically used antidepressant, was labelled with carbon-11 ( t 1 2 = 20.4 min ) as a potential radioligand for the non-invasive assessment of serotonin uptake sites in the human brain with positron emission tomography (PET). The two-step radiochemical synthesis consisted of O-methylation of an amino-protected desmethyl precursor with [ 11C]methyl iodide under mild conditions in the presence of tetrabutylammonium hydroxide in acetonitrile, followed by deprotection with trifluoroacetic acid. 5-[ 11 C]Methoxy-1-[4-( triflouromethyl)-phenyl]-1- pentanone-O-(2- aminoethyl)oxime was obtained in > 98% radiochemical purity in 40 min with a radiochemical yield of 4 ± 2% (non-decay corrected) and a specific radioactivity of 1 ± 0.5 Ci/ μmol. 5-Hydroxy-1-[4-(trifluoromethyl)-phenyl]-1-pentanone- O-[2-( tert-butoxycarbonylamino)ethyl]oxime, the precursor for the radiosynthesis of [ 11C]fluovoxamine, was prepared by a convenient three-step synthesis from the pharmaceutical form of fluvoxamine maleate by converting it into the free base, demethylation by trimethyliodosilane and introduction of the BOC-protective group with di-tert-butyl dicarbonate.
ISSN:0969-8043
1872-9800
DOI:10.1016/S0969-8043(96)00304-1