Synthesis of a radiolabeled charged melatonin receptor ligand

Article abstract of DOI:10.1002/(SICI)1099-1344(199805)41:5<435::AID-JLCR97>3.0.CO;2-L

The synthesis of the first permanently charged melatonin receptor ligand: N-[2-(2-trimethyl-ammoniumethyleneoxy-7- methoxynaphthyl)ethyl]propionamide iodide (2a, TMEPI) and its Carbon-14 analog (2b, ¹⁴C-TMEPI) are described. The ligands can serve as tools to elucidate the mechanism of melatonin receptor regulation. Both compounds 2a and 2b are synthesized in 8 steps. The radiochemical yield and purity of 2b are 99.6 and 99.8% respectively, with specific radioactivity of 716 mCi/mmol.