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

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 cr...

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Bibliographic Details
Published inCentral European journal of chemistry Vol. 11; no. 3; pp. 430 - 437
Main Authors Garadnay, Sándor, Gyulai, Zsuzsanna, Makleit, Sándor, Sipos, Attila
Format Journal Article
LanguageEnglish
Published Heidelberg SP Versita 01.03.2013
Versita
Subjects
Biochemistry
Biological and Medical Physics
Biophysics
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Codeine
Cysteine
Geochemistry
Glutathione
Metabolite
Morphine
Research Article
Morphine
Cysteine
Metabolite
Codeine
Glutathione
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Summary: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
ISSN:1895-1066
2391-5420
1644-3624
2391-5420
DOI:10.2478/s11532-012-0181-4