Voltammetric Oxidation of Drugs of Abuse III. Heroin and Metabolites

The oxidative behavior of heroin in aqueous solution is reported. In order to identify its oxidation peaks, several metabolites, 6‐monoacetylmorphine, 3‐monoacetylmorphine and norheroin, were synthesized and their electrochemical behavior studied using differential pulse voltammetry. The anodic wave...

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Bibliographic Details
Published in:Electroanalysis (New York, N.Y.) N.Y.), 2004-09, Vol.16 (18), p.1497-1502
Main Authors: Garrido, J. M. P. J., Delerue-Matos, C., Borges, F., Macedo, T. R. A., Oliveira-Brett, A. M.
Format: Article
Language:English
Subjects:
3-Monoacetylmorphine
6-Monoacetylmorphine
Drugs of abuse
Heroin
Norheroin
Oxidation
Voltammetry
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Summary:The oxidative behavior of heroin in aqueous solution is reported. In order to identify its oxidation peaks, several metabolites, 6‐monoacetylmorphine, 3‐monoacetylmorphine and norheroin, were synthesized and their electrochemical behavior studied using differential pulse voltammetry. The anodic waves observed for heroin correspond to the oxidation of the tertiary amine group and its follow‐up product (secondary amine), and to the oxidation of the phenolic group obtained from hydrolysis, at alkaline pHs, of the 3‐acetyl group. The results enabled a new oxidative mechanism for heroin to be proposed in which a secondary amine, norheroin, and an aldehyde are obtained. The voltammetric behavior of 6‐monoacetylmorphine and morphine was found to be similar demonstrating that the presence of an acetyl substituent on the 6‐hydroxy group does not have a relevant influence on the peak potential of the wave resulting from oxidation of the 3‐phenolic group.
ISSN:1040-0397
1521-4109
DOI:10.1002/elan.200302975