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N-Demethylation and N-oxidation of thebaine, an isoquinoline alkaloid by Mucor piriformis

Madyastha, KM and Reddy, GVB and Nagarajappa, H and Sridhar, GR (2000) N-Demethylation and N-oxidation of thebaine, an isoquinoline alkaloid by Mucor piriformis. In: Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 39 (05). pp. 377-381.

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Northebaine was identified as the major metabolite formed during the biotransformation of thebaine by Mucor piriformis. Minor metabolites identified are isomeric thebaine N-oxides. Among isomeric thebaine N-oxides, the one with the equatorial oxygen attached to the nitrogen is relatively unstable. Resting cells, grown in the presence of thebaine for 24 hr, efficiently converted thebaine into northebaine (similar to 77% conversion). Similar experiments carried out with northebaine and isomeric thebaine N-oxides as substrates, revealed that while northebaine and the stable thebaine N-oxide are proved to be resistant to further transformation, the unstable thebaine N-oxide nonenzymatically rearranges to 6, 7, 8, 9, 10, 14-hexadehydro-4, 5-epoxy-3, 6-dimethoxy-17-methylthebinan and 6, 7, 8, 9, 10, 14-hexadehydro-3, 6-dimethoxythebinan-4-ol. These studies support the idea that N-demethylation of thebaine is not proceeding via the N-oxide intermediate.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Arun
Date Deposited: 03 Nov 2009 08:45
Last Modified: 03 Nov 2009 08:45
URI: http://eprints.iisc.ac.in/id/eprint/18068

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