Synthesis of 1-(trans-[123I]Iodopropen-2-yl)-4- (4-cyanophenoxymethyl)piperidine: A selective sigma receptor radioligand for SPECT

Article abstract of DOI:10.1002/(SICI)1099-1344(199603)38:3<215::AID-JLCR834>3.0.CO;2-F

1-(trans-[¹²³I]Iodopropen-2-yl)-4-(4-cyanophenoxymethyl)piperidine has been prepared as a novel sigma receptor ligand for SPECT. This ligand was round to be selective in vitro for the sigma receptor site (Ki(σ) = 21.7 nM) when tested in a variety of neuroreceptor binding assays. The lipophilicity or this ligand (log P_7.5 = 3.36) is appropriate for good brain uptake and relatively low non-specific binding. Radioiodination was accomplished using classical electrophilic iododestannylation methods and Specific activity of the purified product was >2100 mCi/μmole. Radiochemical yields were 60-80% EOS and radiochemical purities were >99%. The average time of synthesis and purification was 35 minutes.