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Radiosynthesis of carbon‐11 labelled N‐methyl‐2‐(arylthio)benzylamines: potential radiotracers for the serotonin reuptake receptor
Author(s) -
Wilson Alan A.,
Houle Sylvain
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(19991230)42:13<1277::aid-jlcr284>3.0.co;2-q
Subject(s) - chemistry , radiosynthesis , benzylamine , radioligand , desmethyl , biodistribution , yield (engineering) , metabolite , amine gas treating , carbon 13 nmr , stereochemistry , organic chemistry , positron emission tomography , receptor , in vitro , biochemistry , nuclear medicine , medicine , materials science , metallurgy
The potent and selective serotonin reuptake inhibitor, N,N‐dimethyl‐2‐(2‐amino‐4‐trifluoromethylphenylthio)benzylamine ( 1 ), and a potential metabolite, N‐methyl‐2‐(2‐amino‐4‐trifluoromethylphenylthio)benzyl‐amine ( 2 ) were radiolabelled with Carbon‐11 as potential positron emission tomography (PET) radiotracers. Both [ 11 C]‐( 1 ) and [ 11 C]‐( 2 ) were obtained in good radiochemical yield by alkylation of their respective nor‐methyl precursors with [ 11 C]‐iodomethane in dimethylformamide. Upon HPLC purification and formulation radiochemically pure products were obtained in 25–30% yield (from [ 11 C]‐iodomethane, uncorrected) with specific activities of 25–40 GBq/mole. To further establish the site of labeling, [ 13 C]‐( 1 ) and [ 13 C]‐( 2 ) were also synthesised, using [ 13 C]‐iodomethane, for 13 C NMR analysis. Preliminary biodistribution studies in rats show that both [ 11 C]‐( 1 ) and [ 11 C]‐( 2 ) efficiently and rapidly cross the blood brain barrier. Copyright © 1999 John Wiley & Sons, Ltd.