Design and synthesis of the CB1 selective cannabinoid antagonist AM281: a potential human SPECT ligand

AAPS PharmSci. 1999;1(2):E4. doi: 10.1208/ps010204.

Abstract

In the search for a radioligand capable of imaging cannabinoid CB1 receptors in the living human brain by SPECT (single photon emission computed tomography),N-(morpholin-4-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM281) was synthesized. This compound is an analog of the potent, CB1 receptor selective antagonist SR141716A [N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide]. AM281 bound to brain and spleen membrane preparations (CB1 and CB2 receptors, respectively) with K(i) values of 12 nM and 4200 nM, respectively. AM281 also inhibited the response of guinea-pig small intestine preparation to a cannabinoid receptor agonist. Thus, AM281 behaves as a CB1 receptor selective antagonist. Methods for the rapid, high-yield synthesis and purification of [123I]AM281 were developed, and transaxially reconstructed brain SPECT images obtained after continuous infusion of [123I]AM281 in baboons. Thus [123I]AM281 may be suitable for imaging CB1 receptors in humans.

Publication types

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

MeSH terms

  • Animals
  • Binding, Competitive
  • Cannabinoids / metabolism*
  • Guinea Pigs
  • Humans
  • In Vitro Techniques
  • Intestine, Small / drug effects
  • Intestine, Small / physiology
  • Iodine Radioisotopes
  • Ligands
  • Mice
  • Morpholines / chemical synthesis*
  • Morpholines / metabolism
  • Morpholines / pharmacology
  • Muscle Contraction
  • Muscle, Smooth / drug effects
  • Muscle, Smooth / physiology
  • Papio
  • Prosencephalon / metabolism
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / metabolism
  • Pyrazoles / pharmacology
  • Radioligand Assay
  • Rats
  • Receptor, Cannabinoid, CB2*
  • Receptors, Cannabinoid
  • Receptors, Drug / agonists
  • Receptors, Drug / antagonists & inhibitors*
  • Receptors, Drug / metabolism
  • Spleen / metabolism
  • Tomography, Emission-Computed, Single-Photon

Substances

  • Cannabinoids
  • Cnr2 protein, rat
  • Iodine Radioisotopes
  • Ligands
  • Morpholines
  • Pyrazoles
  • Receptor, Cannabinoid, CB2
  • Receptors, Cannabinoid
  • Receptors, Drug
  • AM 281