Voltammetric oxidation of drugs of abuse III. Heroin and metabolites

Detalhes bibliográficos
Autor(a) principal: Garrido, Jorge
Data de Publicação: 2004
Outros Autores: Delerue-Matos, Cristina, Borges, F., Macedo, Tice R. A., Oliveira-Brett, A. M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.22/2935
Resumo: 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.
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spelling Voltammetric oxidation of drugs of abuse III. Heroin and metabolitesHeroin3-Monoacetylmorphine6-MonoacetylmorphineNorheroinOxidationVoltammetryDrugs of abuseThe 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.WILEY-VCH VerlagRepositório Científico do Instituto Politécnico do PortoGarrido, JorgeDelerue-Matos, CristinaBorges, F.Macedo, Tice R. A.Oliveira-Brett, A. M.2013-11-22T16:08:04Z20042004-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.22/2935eng10.1002/elan.200302975info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-03-13T12:42:32Zoai:recipp.ipp.pt:10400.22/2935Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T17:23:57.523561Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
title Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
spellingShingle Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
Garrido, Jorge
Heroin
3-Monoacetylmorphine
6-Monoacetylmorphine
Norheroin
Oxidation
Voltammetry
Drugs of abuse
title_short Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
title_full Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
title_fullStr Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
title_full_unstemmed Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
title_sort Voltammetric oxidation of drugs of abuse III. Heroin and metabolites
author Garrido, Jorge
author_facet Garrido, Jorge
Delerue-Matos, Cristina
Borges, F.
Macedo, Tice R. A.
Oliveira-Brett, A. M.
author_role author
author2 Delerue-Matos, Cristina
Borges, F.
Macedo, Tice R. A.
Oliveira-Brett, A. M.
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Repositório Científico do Instituto Politécnico do Porto
dc.contributor.author.fl_str_mv Garrido, Jorge
Delerue-Matos, Cristina
Borges, F.
Macedo, Tice R. A.
Oliveira-Brett, A. M.
dc.subject.por.fl_str_mv Heroin
3-Monoacetylmorphine
6-Monoacetylmorphine
Norheroin
Oxidation
Voltammetry
Drugs of abuse
topic Heroin
3-Monoacetylmorphine
6-Monoacetylmorphine
Norheroin
Oxidation
Voltammetry
Drugs of abuse
description 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.
publishDate 2004
dc.date.none.fl_str_mv 2004
2004-01-01T00:00:00Z
2013-11-22T16:08:04Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10400.22/2935
url http://hdl.handle.net/10400.22/2935
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1002/elan.200302975
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv WILEY-VCH Verlag
publisher.none.fl_str_mv WILEY-VCH Verlag
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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