Comparison of the behavioral and neurochemical effects of the two optical enantiomers of medetomidine, a selective alpha-2-adrenoceptor agonist

J Pharmacol Exp Ther. 1991 Nov;259(2):848-54.

Abstract

Medetomidine (MED) is a veterinary sedative whose mode of action is activation of alpha-2 adrenoceptors. Because the carbon atom which separates the two ring systems is methylated, there is a center of stereochemical asymmetry in the molecule. The resulting enantiomers, d-MED and l-MED have recently become available for study. The biological activity of MED, as is now demonstrated in rats in vivo, seems to reside almost exclusively in the d-MED form. Only at extremely high doses (e.g., 10 mg/kg) does l-MED exert any effects, interpreted as alpha-2 adrenoceptor antagonism. In contrast, doses of d-MED as low as 30 micrograms/kg cause sedation, hypothermia and induce neurochemical changes in norepinephrine and 5-hydroxytryptamine metabolism in brain characteristic of alpha-2-agonists (decreases in concentrations of biogenic amine metabolites, turnover and increases in concentration of parent amine). The most sensitive neurochemical indicator of the alpha-2-agonist action of d-MED was the concentration of unconjugated 3-methoxy-4-hydroxy-phenyethylene glycol in rat cerebral spinal fluid, doses of d-MED as low as 10 micrograms/kg caused a significant reduction in this norepinephrine metabolite. Simultaneous administration of the specific alpha-2 adrenoceptor antagonist, atipamezole (1 mg/kg), effectively inhibited the behavioral and most of the neurochemical actions of d-MED (100 micrograms/kg). It is concluded that the enantiomers of MED may be extremely useful in elucidating structure action relationships at alpha-2 adrenoceptors.

Publication types

  • Comparative Study

MeSH terms

  • Adrenergic alpha-Agonists / pharmacology*
  • Adrenergic alpha-Antagonists / pharmacology
  • Amines / cerebrospinal fluid
  • Animals
  • Behavior, Animal / drug effects*
  • Brain / drug effects*
  • Brain / physiology
  • Imidazoles / pharmacology*
  • Medetomidine
  • Methoxyhydroxyphenylglycol / analogs & derivatives
  • Methoxyhydroxyphenylglycol / metabolism
  • Methyltyrosines / pharmacology
  • Mice
  • Norepinephrine / metabolism
  • Rats
  • Rats, Inbred Strains
  • Stereoisomerism

Substances

  • Adrenergic alpha-Agonists
  • Adrenergic alpha-Antagonists
  • Amines
  • Imidazoles
  • Methyltyrosines
  • 3-methoxy-4-hydroxyphenylglycol sulfate
  • alpha-methyltyrosine methyl ester
  • Methoxyhydroxyphenylglycol
  • Medetomidine
  • Norepinephrine