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

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Abstract

5-Methoxy-1-[4-(trifluoromethyl)-phenyl]-1-pentanone-O-(2-aminoethyl)oxime (fluvoxamine), a potent clinically used antidepressant, was labelled with carbon-11 (t12 = 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-[11C]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.

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    Effect of trifluoromethyl on bioactive molecules widens the prospect of organofluorine chemistry in Pharmacology [18]. Antidepressants like Prozac (fluoxetine) [19] and Luvox (fluvoxamine) [20], contain a para-phenyl trifluoromethyl group. Also, famous antiprotozoal drug, Lariam (Mefloquine) has two trifluoromethyl groups, on each of the aromatic rings of a quinoline nucleus [21].

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