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Pharmaceutisch Weekblad

, Volume 5, Issue 4, pp 159–164 | Cite as

Enzymatic O-methylation of the dopamine agonist dipropyl-5,6-dihydroxy-aminotetralin: isolation and structure elucidation of the O-methylated metabolite

  • H. Rollema
  • C. J. Grol
Original Articles

Abstract

The (+)-enantiomer of the potent dopamine agonist dipropyl-5,6-dihydroxyaminotetralin (DP-5,6-diOH-ATN) is metabolizedin vitro by catechol-O-methyltransferase (comt) to oneO-methyl derivative. This compound was isolated from the incubation mixture by reversedphasehplc, after the incubation mixture had been purified over Sephadex G 10 columns and the excess parent catecholamine had been removed with alumina. One of the possibleO-methyl metabolites, dipropyl-5-hydroxy-6-methoxyaminotetralin, was synthesized from dipropyl-5,6-dimethoxyaminotetralin by a regioselective mono-demeth-ylation with iodotrimethylsilane. Comparison of Chromatographic and spectral data of the products from incubation and synthesis showed that different isomers are formed;i.e. DP-5,6-diOH-ATN is exclusively meta-O-methylated bycomtin vitro to dipropyl-5-methoxy-6-hydroxyaminotetralin.

Keywords

Public Health Alumina Internal Medicine Dopamine Catecholamine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Royal Dutch Association for Advancement of Pharmacy 1983

Authors and Affiliations

  • H. Rollema
    • 1
  • C. J. Grol
    • 1
  1. 1.Department of Medicinal Chemistry, Laboratory of Pharmaceutical and Analytical ChemistryState University of GroningenAW GroningenThe Netherlands

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