In the presence of thiols, the methanesulfonic acid-catalyzed rearrangement of thebaine (7), or N-(n-propyl)northebaine (8) is accompanied by nucleophilic substitution and O-demethylation to furnish the corresponding 2-(alkylthio)aporphines (9, 10, 11, 12). Actions of these derivatives on the dopaminergic system are similar to apomorphine and N-(n-propyl)-norapomorphine, except the S-enantiomer ((S)-9) which was much less active.
|Number of pages||10|
|Journal||Medicinal Chemistry Research|
|Publication status||Published - Dec 1 1997|
ASJC Scopus subject areas
- Pharmacology, Toxicology and Pharmaceutics(all)
- Organic Chemistry