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


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.


Public Health Alumina Internal Medicine Dopamine Catecholamine 
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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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