First synthesis of important secondary oxidative metabolites of morphine and codeine with the Michael addition

• Authors: Sándor Garadnay , Zsuzsanna Gyulai , Sándor Makleit , Attila Sipos
• Languages of publication: EN

Abstracts

EN

Abstract Morphine (1) and codeine (2) are two representatives of medically important, frequently used natural opiates, therefore the exploration of their metabolic pathways and the exact characterization of the metabolites are main targets of their pharmacological studies. These morphinans also play a crucial role in drug abuse; therefore, the analysis and preparation of the metabolites for identification and quantitation in human samples are considered important aims. In order to allow the in-depth analysis of metabolites derived from the oxidative pathways through morphinone (3) and codeinone (4), synthetic procedures have been elaborated for the gram-scale preparation of glutathione and N-acetylcysteine adducts. Primary pharmacological studies revealed the inactive nature of these metabolites in opioid receptor binding tests. Graphical abstract [...]

Keywords

EN

Morphine; Codeine; Metabolite; Glutathione; Cysteine

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 3
• Pages: 430-437

Dates

published

1 - 3 - 2013

online

28 - 12 - 2012

Contributors

author

Sándor Garadnay

• Department of Organic Chemistry, University of Debrecen, H-4032, Debrecen, Hungary

author

Zsuzsanna Gyulai

• Department of Organic Chemistry, University of Debrecen, H-4032, Debrecen, Hungary

author

Sándor Makleit

• Department of Organic Chemistry, University of Debrecen, H-4032, Debrecen, Hungary

author

Attila Sipos

• Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, H-4032, Debrecen, Hungary

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Identifiers

DOI

10.2478/s11532-012-0181-4