Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine

Detalhes bibliográficos
Autor(a) principal: Novák,Michal
Data de Publicação: 2011
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000400004
Resumo: The thermal elimination of benzoic acid from (-)-cocaine is shown to be temperature-dependent. In the temperature range of 200-500 °C only a trans-elimination is observed leading to methylecgonidine. Above ca. 500 °C a second mechanism, the cis-elimination, comes up yielding a novel alkaloid methylisoecgonidine which has been characterized by means of mass spectrometry. At 600 °C the cis-elimination predominates. The trans-elimination is postulated a two-step process consisting of a 1,7- and a 1,5-hydrogen shift. The chemistry of cocaine base smoking is explained using the theory of chemical activation.
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spelling Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocainecocaine base smoking(+)-pseudococaine1,3-methoxyl shiftThe thermal elimination of benzoic acid from (-)-cocaine is shown to be temperature-dependent. In the temperature range of 200-500 °C only a trans-elimination is observed leading to methylecgonidine. Above ca. 500 °C a second mechanism, the cis-elimination, comes up yielding a novel alkaloid methylisoecgonidine which has been characterized by means of mass spectrometry. At 600 °C the cis-elimination predominates. The trans-elimination is postulated a two-step process consisting of a 1,7- and a 1,5-hydrogen shift. The chemistry of cocaine base smoking is explained using the theory of chemical activation.Sociedade Brasileira de Química2011-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000400004Química Nova v.34 n.4 2011reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422011000400004info:eu-repo/semantics/openAccessNovák,Michaleng2011-05-20T00:00:00Zoai:scielo:S0100-40422011000400004Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2011-05-20T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
title Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
spellingShingle Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
Novák,Michal
cocaine base smoking
(+)-pseudococaine
1,3-methoxyl shift
title_short Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
title_full Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
title_fullStr Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
title_full_unstemmed Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
title_sort Temperature-dependent benzoic acid elimination mechanisms in pyrolysis of (-)-cocaine
author Novák,Michal
author_facet Novák,Michal
author_role author
dc.contributor.author.fl_str_mv Novák,Michal
dc.subject.por.fl_str_mv cocaine base smoking
(+)-pseudococaine
1,3-methoxyl shift
topic cocaine base smoking
(+)-pseudococaine
1,3-methoxyl shift
description The thermal elimination of benzoic acid from (-)-cocaine is shown to be temperature-dependent. In the temperature range of 200-500 °C only a trans-elimination is observed leading to methylecgonidine. Above ca. 500 °C a second mechanism, the cis-elimination, comes up yielding a novel alkaloid methylisoecgonidine which has been characterized by means of mass spectrometry. At 600 °C the cis-elimination predominates. The trans-elimination is postulated a two-step process consisting of a 1,7- and a 1,5-hydrogen shift. The chemistry of cocaine base smoking is explained using the theory of chemical activation.
publishDate 2011
dc.date.none.fl_str_mv 2011-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000400004
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422011000400004
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0100-40422011000400004
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Química Nova v.34 n.4 2011
reponame:Química Nova (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Química Nova (Online)
collection Química Nova (Online)
repository.name.fl_str_mv Química Nova (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv quimicanova@sbq.org.br
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