International Journal of Pure and Applied Chemistry (IJPAC)

 

6. Molecular modelling analysis of the metabolism of morphine

Fazlul Huq

School of Biomedical Sciences, Faculty of Health Sciences, The University of Sydney

E-mail : f.huq@fhs.usyd.edu.au.

 

Abstract:

Molecular modelling analyses based on molecular mechanics, semi-empirical (PM3) and DFT (at B3LYP/6-31G* level) calculations show that morphine and its metabolites have similar LUMO-HOMO energy differences except MN which has a much lower value indicating its greater kinetic lability. The greater kinetic lability of morphinone and its binding with sulfur-containing antioxidants glutathione, metalothionein and cysteine and the resulting alteration of the antioxidant status of the cell explain why the metabolite is much more toxic than morphine itself. The presence of multiple charged and neutral regions on the surface of morphine and M6G can be seen to support the idea of their multiple sites interaction with opioid receptors.

 

Key words: Morphine, cancer, palliative care, morphinone, toxicity, molecular modelling

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