Synthesis of [2-{(4-chlorophenyl)(4-[125I]iodophenyl)} methoxyethyl]-1-piperidine-3-carboxylic acid, [125I]CIPCA: A potential radiotracer for GABA uptake sites

Article abstract of DOI:10.1002/jlcr.2580361008

The synthesis of racemic [2-{(4-Chlorophenyl)(4-iodophenyl)} methoxyethyl]-1-piperidine-3-carboxylic acid, (CIPCA) and its radioiodinated analog [¹²⁵]CIPCA is described. CIPCA was synthesized from 4-iodobenzoyl chloride in five steps in 16% overall yield. Ammonium sulfate catalyzed solid-state isotopic exchange of CIPCA with Na¹²⁵I provided [¹²⁵I]CIPCA in 34% isolated radiochemical yield at a specific activity of 118 Ci/mmol. [¹²⁵I]CIPCA demonstrated moderate brain extraction and good in vivo radiostability in preliminary biodistribution studies conducted in CD-1 mice. [¹²⁵I]CIPCA is a potentially useful radiotracer for study of the GABA uptake system.