N-methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-salsolinol, in rat brains: in vivo microdialysis study

J Neurochem. 1992 Aug;59(2):395-400. doi: 10.1111/j.1471-4159.1992.tb09384.x.

Abstract

N-Methylation of (R)-1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [(R)-salsolinol] derived from dopamine was proved by in vivo microdialysis study in the rat brain. The striatum was perfused with (R)-salsolinol and N-methylated compound was identified in the dialysate using HPLC and electrochemical detection with multichanneled electrodes. N-Methylation of (R)-salsolinol was confirmed in three other regions of the brain, the substantia nigra, hypothalamus, and hippocampus. In the substantia nigra, the amount of N-methylated (R)-salsolinol was significantly larger than in the other three regions. These results indicate that around dopaminergic neurons, particularly in the substantia nigra, (R)-salsolinol was methylated into N-methyl-(R)-salsolinol, which has a chemical structure similar to that of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, the selective dopaminergic neurotoxin. N-Methylation of tetrahydroisoquinolines and beta-carbolines have already been proven to increase their toxicity to dopaminergic neurons and N-methylation might be an essential step for these alkaloids to increase their toxicity. On the other hand, after perfusion of (R)-salsolinol, release of dopamine and 5-hydroxytryptamine was observed and inhibition of monoamine oxidase was indicated. (R)-Salsolinol and its derivatives may be candidates for being dopaminergic neurotoxins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Brain / metabolism*
  • Brain Chemistry
  • Chromatography, High Pressure Liquid
  • Dialysis / methods
  • Dopamine / analysis
  • Dopamine / metabolism*
  • Hippocampus / chemistry
  • Hippocampus / metabolism
  • Hypothalamus / chemistry
  • Hypothalamus / metabolism
  • Isoquinolines / analysis
  • Isoquinolines / metabolism*
  • Male
  • Methylation
  • Rats
  • Rats, Inbred Strains
  • Substantia Nigra / chemistry
  • Substantia Nigra / metabolism
  • Tetrahydroisoquinolines*

Substances

  • Isoquinolines
  • Tetrahydroisoquinolines
  • 1,2,3,4-tetrahydroisoquinoline
  • salsolinol
  • Dopamine