High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand

Bioorg Med Chem. 2008 Jun 1;16(11):6116-23. doi: 10.1016/j.bmc.2008.04.050. Epub 2008 Apr 25.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Binding Sites
  • Cell Line
  • Cell Line, Tumor
  • DNA-Binding Proteins
  • Ethylamines / chemical synthesis*
  • Ethylamines / metabolism
  • Humans
  • Intracellular Signaling Peptides and Proteins / genetics
  • Intracellular Signaling Peptides and Proteins / metabolism
  • Iodine Radioisotopes / metabolism
  • Iodobenzenes / chemical synthesis*
  • Iodobenzenes / metabolism
  • Ketanserin / metabolism
  • Ketanserin / pharmacology
  • Nuclear Proteins / biosynthesis
  • Nuclear Proteins / genetics
  • Nuclear Proteins / metabolism
  • Radioligand Assay
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / metabolism*
  • Receptor, Serotonin, 5-HT2A / metabolism*
  • Serotonin 5-HT2 Receptor Agonists*
  • Serotonin 5-HT2 Receptor Antagonists
  • Tritium
  • Tumor Necrosis Factor alpha-Induced Protein 3

Substances

  • DNA-Binding Proteins
  • Ethylamines
  • Intracellular Signaling Peptides and Proteins
  • Iodine Radioisotopes
  • Iodobenzenes
  • N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine
  • Nuclear Proteins
  • Radiopharmaceuticals
  • Receptor, Serotonin, 5-HT2A
  • Serotonin 5-HT2 Receptor Agonists
  • Serotonin 5-HT2 Receptor Antagonists
  • Tritium
  • Ketanserin
  • TNFAIP3 protein, human
  • Tumor Necrosis Factor alpha-Induced Protein 3