High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand.
The title compound ([3H]INBMeO) was prepared by an O,O-dimethylation reaction of a t-BOC protected diphenolic precursor using no carrier added tritiated iodomethane in DMF with K(2)CO(3). Removal of the t-BOC protecting group and purification by HPLC afforded an overall yield of 43%, with a radiochemical purity of 99% and specific activity of 164Ci/mmol. The new radioligand was suitable for labeling human 5-HT(2A) receptors in two heterologous cell lines and had about 20-fold higher affinity than [(3)H]ketanserin.
Nichols
David E
DE
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, Purdue University, 1333 Robert E. Heine Pharmacy Building, West Lafayette, IN 47907, USA. drdave@pharmacy.purdue.edu
Frescas
Stewart P
SP
Chemel
Benjamin R
BR
Rehder
Kenneth S
KS
Zhong
Desong
D
Lewin
Anita H
AH
D001665:Binding Sites; D002460:Cell Line; D045744:Cell Line, Tumor; D004268:DNA-Binding Proteins; D005021:Ethylamines / Q000138:chemical synthesis* / Q000378:metabolism; D006801:Humans; D047908:Intracellular Signaling Peptides and Proteins / Q000235:genetics / Q000378:metabolism; D007457:Iodine Radioisotopes / Q000378:metabolism; D007462:Iodobenzenes / Q000138:chemical synthesis* / Q000378:metabolism; D007650:Ketanserin / Q000378:metabolism / Q000494:pharmacology; D009687:Nuclear Proteins / Q000096:biosynthesis / Q000235:genetics / Q000378:metabolism; D011869:Radioligand Assay; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000378:metabolism*; D044402:Receptor, Serotonin, 5-HT2A / Q000378:metabolism*; D058826:Serotonin 5-HT2 Receptor Agonists; D058830:Serotonin 5-HT2 Receptor Antagonists; D014316:Tritium; D000072598:Tumor Necrosis Factor alpha-Induced Protein 3
D004268:DNA-Binding Proteins; D005021:Ethylamines; D047908:Intracellular Signaling Peptides and Proteins; D007457:Iodine Radioisotopes; D007462:Iodobenzenes; C531104:N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine; D009687:Nuclear Proteins; D019275:Radiopharmaceuticals; D044402:Receptor, Serotonin, 5-HT2A; D058826:Serotonin 5-HT2 Receptor Agonists; D058830:Serotonin 5-HT2 Receptor Antagonists; D014316:Tritium; D007650:Ketanserin; C076529:TNFAIP3 protein, human; D000072598:Tumor Necrosis Factor alpha-Induced Protein 3