R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue

J Med Chem. 1991 Jan;34(1):24-8. doi: 10.1021/jm00105a005.


The R-(-)- and S-(+)-enantiomers of 11-hydroxy-N-allyl (4), and 10,11-dihydroxy-N-allyl (3) congeners of 11-hydroxy-N-n-propylnorapomorphine (11-OH-NPa, 2) or N-n-propylnorapomorphine (NPA, 1) were synthesized. Binding affinity of these compounds at dopamine (DA) receptor sites was evaluated with a membrane preparation of corpus striatum from rat brain. The R/S enantiomeric receptor affinity ratio was enhanced by allylic substitution of 3 and 4 and their R isomers had high DA receptor affinity similar to that of the N-n-propyl congeners. These N-allylnoraporphines are proposed as useful precursors to the preparation of their tritiated N-n-propyl enantiomers.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Aporphines / chemical synthesis*
  • Aporphines / chemistry
  • Aporphines / metabolism
  • Corpus Striatum / metabolism*
  • Dopamine Agents / chemical synthesis*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Rats
  • Receptors, Dopamine / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship


  • Aporphines
  • Dopamine Agents
  • Indicators and Reagents
  • Receptors, Dopamine
  • 11-hydroxy-N-allylnoraporphine
  • 10,11-dihydroxy-N-allylnoraporphine