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Preparation of iodine‐123 labeled AM251: A potential SPECT radioligand for the brain cannabinoid CB1 receptor
Author(s) -
Lan Ruoxi,
Gatley S. John,
Makriyannis Alexandros
Publication year - 1996
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(199610)38:10<875::aid-jlcr908>3.0.co;2-g
Subject(s) - am251 , chemistry , radioligand , cannabinoid receptor , chloramine t , cannabinoid , iodine , radiosynthesis , yield (engineering) , biodistribution , iodine monochloride , iodide , antagonist , sonogashira coupling , stereochemistry , pharmacology , receptor , organic chemistry , in vivo , biochemistry , in vitro , medicine , materials science , microbiology and biotechnology , metallurgy , biology , palladium , catalysis
We report the synthesis and labeling with iodine‐123 of N‐(piperidin‐1‐yl)‐5‐(4‐iodophenyl)‐1‐(2,4‐dichlorophenyl)‐4‐methyl‐1H‐pyrazole‐3‐carboxamide (AM251). This compound is an analog of the recently described cannabinoid receptor antagonist, SR141716A, in which a 4‐chlorophenyl group is replaced by 4‐iodophenyl. Labeling in good yield (62%) and radiochemical purity (< 95%), and high specific activity (< 2500 Ci/mmol) was achieved by an iododestannylation reaction using the tributyltin precursor, no carrier added I‐123 iodide, and chloramine‐T.