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Advisor(s)
Abstract(s)
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.
Description
Keywords
Heroin 3-Monoacetylmorphine 6-Monoacetylmorphine Norheroin Oxidation Voltammetry Drugs of abuse
Citation
Publisher
WILEY-VCH Verlag