Synthesis and affinity of a possible byproduct of electrophilic radiolabeling of [123I]IBZM

Bioorg Med Chem Lett. 2003 Nov 17;13(22):4015-7. doi: 10.1016/j.bmcl.2003.08.063.

Abstract

The iodobenzamide neuroleptic analogue (S)-N-(1-ethylpyrrolidin-2-ylmethyl)-2-hydroxy-5-iodo-6-methoxybenzamide (5-IBZM) was synthesized stereospecifically and its pharmacological properties were compared with the 3-iodo isomer (IBZM) used for imaging D(2) receptors in vivo. The isomer 5-IBZM had 100-fold lower affinity than IBZM and migrated with similar retention time as the byproduct formed during electrophilic iodination of BZM.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzamides / chemical synthesis*
  • Benzamides / pharmacokinetics
  • Indicators and Reagents
  • Iodine Radioisotopes*
  • Isotope Labeling / methods
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / pharmacokinetics
  • Structure-Activity Relationship

Substances

  • Benzamides
  • Indicators and Reagents
  • Iodine Radioisotopes
  • Pyrrolidines
  • 3-iodo-2-hydroxy-6-methoxy-N-((1-ethyl-2-pyrrolidinyl)methyl)benzamide