(+/-)alpha-Phenyl-beta-(3,4-dimethoxy)- and (+/-)alpha-phenyl-beta -(3,4-dihydroxy)phenethylamines: potential probes for nicotinic acetylcholine receptor-ion channel molecule from torpedo electric organ

J Pharm Sci. 1987 Oct;76(10):830-3. doi: 10.1002/jps.2600761017.

Abstract

The synthesis of some N-methyl, N-alkyl derivatives of (+/-)alpha-phenyl-beta-(3,4-dimethoxy)- and (+/-)alpha-phenyl-beta-(3,4-dihydroxy)-phenethylamines was achieved. These compounds were shown to bear certain structural features of acetylcholine (ACh), as well as phencyclidine (PCP). The latter was reported to act as a specific probe for the nicotinic ACh receptor-ion channel molecule from Torpedo electric organ. Biochemical binding studies revealed that for the nicotinic ACh receptor, the 3,4-dimethoxy derivatives behaved as blockers for the binding interaction of [3H]ACh, whereas the 3,4-dihydroxy analogues stimulated such binding. On the other hand, all of the tested phenethylamines exhibited potent blockade towards [3H]PCP binding interactions. The results indicated that the tested compounds might be applied as potential probes for the ACh receptor-ion channel molecule.

MeSH terms

  • Acetylcholine / metabolism
  • Animals
  • Electric Organ / analysis*
  • In Vitro Techniques
  • Phenethylamines / chemical synthesis*
  • Receptors, Cholinergic / analysis*
  • Torpedo

Substances

  • Phenethylamines
  • Receptors, Cholinergic
  • Acetylcholine