Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas

Detalhes bibliográficos
Autor(a) principal: Miossi, Karoline Pereira
Data de Publicação: 2024
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)
Texto Completo: http://repositorio.ufes.br/handle/10/17397
Resumo: During the year, the police seize tons of illegal drugs, such as crack and cocaine. In accordance with Law No. 12,961, art. 50-A, all seized drugs must be disposed of by incineration. On the other hand, the area of forensic chemistry has been growing and requiring increasingly efficient analysis and quantification methods. One of the objectives of this work is to compare three cocaine quantification methods: gas chromatography coupled with mass spectrometry (GC/MS), high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR). The second objective of the work is to present methodologies for obtaining reference materials (MF) for cocaine and its metabolites, from seized street crack samples. MF’s are widely used in toxicological tests (for example, doping) and in research. Since drugs are incinerated, they can be reused, like crack. Therefore, for the first, 10 samples of crack and 10 samples of street cocaine seized by the Civil Police of the State of Espírito Santo (PC-ES) were analyzed, from which the correlation coefficient (R) for the CG/EM was determined. (R = 0.9939) and HPLC (crack: R = 0.9984; cocaine: R = 0.9907). A slight difference in cocaine percentages was observed between methods. For the second objective, he isolated the cocaine present in crack and with it, through semisynthesis, synthesized the main metabolites of cocaine (ecgonine methyl ester, ecgonine and cinnamoylecgonine). The products were analyzed using NMR, GC/MS and HPLC spectroscopy techniques and Fourier transform infrared spectroscopy (FTVI) aiming to characterize and determine their purity. Therefore, the cocaine found in crack is 48.34%. For the isolation of cocaine, liquid chromatography and crystallization/recrystallization were used. For the synthesis of ecgonine, three acid hydrolysis was carried out, varying the starting material, with: pure crack, cocaine obtained by liquid chromatography and cocaine obtained by recrystallization. The latter is quantified by HPLC and NMR. From the ecgonine obtained, ecgonine methyl ester and cinnamoylecgonine were synthesized by acid catalytic esterification.
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spelling Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas ApreendidasSynthesis of cocaine metabolites and studies of analytical methods from learned drugsCocaínacrackmateriais de referênciasquantificarecgoninametil éster ecgoninacinamoilecgoninasubject.br-rjbnÁrea(s) do conhecimento do documento (Tabela CNPq)During the year, the police seize tons of illegal drugs, such as crack and cocaine. In accordance with Law No. 12,961, art. 50-A, all seized drugs must be disposed of by incineration. On the other hand, the area of forensic chemistry has been growing and requiring increasingly efficient analysis and quantification methods. One of the objectives of this work is to compare three cocaine quantification methods: gas chromatography coupled with mass spectrometry (GC/MS), high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR). The second objective of the work is to present methodologies for obtaining reference materials (MF) for cocaine and its metabolites, from seized street crack samples. MF’s are widely used in toxicological tests (for example, doping) and in research. Since drugs are incinerated, they can be reused, like crack. Therefore, for the first, 10 samples of crack and 10 samples of street cocaine seized by the Civil Police of the State of Espírito Santo (PC-ES) were analyzed, from which the correlation coefficient (R) for the CG/EM was determined. (R = 0.9939) and HPLC (crack: R = 0.9984; cocaine: R = 0.9907). A slight difference in cocaine percentages was observed between methods. For the second objective, he isolated the cocaine present in crack and with it, through semisynthesis, synthesized the main metabolites of cocaine (ecgonine methyl ester, ecgonine and cinnamoylecgonine). The products were analyzed using NMR, GC/MS and HPLC spectroscopy techniques and Fourier transform infrared spectroscopy (FTVI) aiming to characterize and determine their purity. Therefore, the cocaine found in crack is 48.34%. For the isolation of cocaine, liquid chromatography and crystallization/recrystallization were used. For the synthesis of ecgonine, three acid hydrolysis was carried out, varying the starting material, with: pure crack, cocaine obtained by liquid chromatography and cocaine obtained by recrystallization. The latter is quantified by HPLC and NMR. From the ecgonine obtained, ecgonine methyl ester and cinnamoylecgonine were synthesized by acid catalytic esterification.Durante o ano, a polícia apreende toneladas de drogas ilegais, como o crack e a cocaína. De acordo com Lei nº 12.961, art. 50-A, todas as drogas apreendidas devem ser descartas por incineração. Por outro lado, área da química forense vem crescendo e necessitando de métodos de análises e quantificações cada vez mais eficiente. Este trabalho tem como um de seus objetivos, comparar três métodos de quantificação de cocaína: a cromatografia gasosa acoplada com espectrometria de massas (CG/EM), a cromatografia líquida de alta eficiência (CLAE) e o ressonância magnética nuclear (RMN). O segundo objetivos do trabalho é apresenta metodologias para obtenção de materiais de referências (MF) para cocaína e seus metabólitos, a partir das amostras de crack de rua apreendidas. Os MF’s são muito utilizados em exames toxicológicos (por exemplo, doping) e na área de pesquisas. Visto que as drogas são incineradas, pode-se realizar o reaproveitamento delas, como o crack. Sendo assim, para o primeiro, foram analisadas 10 amostras de crack e 10 amostras de cocaína de rua apreendias pela Polícia Civil do Estado do Espírito Santo (PC-ES), do qual determinou o coeficiente de correlação (R) para o CG/EM (R = 0,9939) e o CLAE (crack: R = 0,9984; cocaína: R = 0,9907). Observou-se uma ligeira diferença nas porcentagens de cocaína entre os métodos. Para o segundo objetivo, isolou a cocaína presente no crack e com a mesma, por meio de uma semi síntese, sintetizou os principais metabólitos da cocaína (metil éster ecgonina, ecgonina e cinamoilecgonina). Os produtos foram analisados pelas técnicas de espectroscopia de RMN, CG/EM e CLAE e espectroscopia no infravermelho por transformada de Fourier (IVTF) objetivando a caracterização e determinação de sua pureza. Com isso, a cocaína encontrada no crack é 48,34%. Para o isolamento da cocaína utilizou-se cromatografia liquida e a cristalização/recristalização. Para síntese da ecgonina foi realizado três hidrolise ácida, variando o material de partida, com: o crack puro, cocaína obtido pela cromatografia liquida e a cocaína obtido por recristalização. Sendo a última quantificada por CLAE e por RMN. A partir da ecgonina obtida, sintetizou-se a metil éster ecgonina e a cinamoilecgonina por uma esterificação de catálise ácida.CAPESUniversidade Federal do Espírito SantoBRMestrado em QuímicaCentro de Ciências ExatasUFESPrograma de Pós-Graduação em QuímicaCunha Neto, Álvarohttps://orcid.org/0000-0002-1814-6214http://lattes.cnpq.br/7448379486432052https://orcid.org/0009-0001-4966-0849http://lattes.cnpq.br/1952753362670671Kuster, Ricardo Machadohttps://orcid.org/0000-0002-8961-5348http://lattes.cnpq.br/4149814906786366França, Hildegardo Seiberthttps://orcid.org/0000-0001-6129-8793http://lattes.cnpq.br/1284874997224988Miossi, Karoline Pereira2024-06-19T12:49:20Z2024-06-19T12:49:20Z2024-03-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisTextapplication/pdfhttp://repositorio.ufes.br/handle/10/17397porinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)instname:Universidade Federal do Espírito Santo (UFES)instacron:UFES2024-08-29T11:25:10Zoai:repositorio.ufes.br:10/17397Repositório InstitucionalPUBhttp://repositorio.ufes.br/oai/requestopendoar:21082024-08-29T11:25:10Repositório Institucional da Universidade Federal do Espírito Santo (riUfes) - Universidade Federal do Espírito Santo (UFES)false
dc.title.none.fl_str_mv Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
Synthesis of cocaine metabolites and studies of analytical methods from learned drugs
title Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
spellingShingle Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
Miossi, Karoline Pereira
Cocaína
crack
materiais de referências
quantificar
ecgonina
metil éster ecgonina
cinamoilecgonina
subject.br-rjbn
Área(s) do conhecimento do documento (Tabela CNPq)
title_short Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
title_full Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
title_fullStr Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
title_full_unstemmed Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
title_sort Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
author Miossi, Karoline Pereira
author_facet Miossi, Karoline Pereira
author_role author
dc.contributor.none.fl_str_mv Cunha Neto, Álvaro
https://orcid.org/0000-0002-1814-6214
http://lattes.cnpq.br/7448379486432052
https://orcid.org/0009-0001-4966-0849
http://lattes.cnpq.br/1952753362670671
Kuster, Ricardo Machado
https://orcid.org/0000-0002-8961-5348
http://lattes.cnpq.br/4149814906786366
França, Hildegardo Seibert
https://orcid.org/0000-0001-6129-8793
http://lattes.cnpq.br/1284874997224988
dc.contributor.author.fl_str_mv Miossi, Karoline Pereira
dc.subject.por.fl_str_mv Cocaína
crack
materiais de referências
quantificar
ecgonina
metil éster ecgonina
cinamoilecgonina
subject.br-rjbn
Área(s) do conhecimento do documento (Tabela CNPq)
topic Cocaína
crack
materiais de referências
quantificar
ecgonina
metil éster ecgonina
cinamoilecgonina
subject.br-rjbn
Área(s) do conhecimento do documento (Tabela CNPq)
description During the year, the police seize tons of illegal drugs, such as crack and cocaine. In accordance with Law No. 12,961, art. 50-A, all seized drugs must be disposed of by incineration. On the other hand, the area of forensic chemistry has been growing and requiring increasingly efficient analysis and quantification methods. One of the objectives of this work is to compare three cocaine quantification methods: gas chromatography coupled with mass spectrometry (GC/MS), high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR). The second objective of the work is to present methodologies for obtaining reference materials (MF) for cocaine and its metabolites, from seized street crack samples. MF’s are widely used in toxicological tests (for example, doping) and in research. Since drugs are incinerated, they can be reused, like crack. Therefore, for the first, 10 samples of crack and 10 samples of street cocaine seized by the Civil Police of the State of Espírito Santo (PC-ES) were analyzed, from which the correlation coefficient (R) for the CG/EM was determined. (R = 0.9939) and HPLC (crack: R = 0.9984; cocaine: R = 0.9907). A slight difference in cocaine percentages was observed between methods. For the second objective, he isolated the cocaine present in crack and with it, through semisynthesis, synthesized the main metabolites of cocaine (ecgonine methyl ester, ecgonine and cinnamoylecgonine). The products were analyzed using NMR, GC/MS and HPLC spectroscopy techniques and Fourier transform infrared spectroscopy (FTVI) aiming to characterize and determine their purity. Therefore, the cocaine found in crack is 48.34%. For the isolation of cocaine, liquid chromatography and crystallization/recrystallization were used. For the synthesis of ecgonine, three acid hydrolysis was carried out, varying the starting material, with: pure crack, cocaine obtained by liquid chromatography and cocaine obtained by recrystallization. The latter is quantified by HPLC and NMR. From the ecgonine obtained, ecgonine methyl ester and cinnamoylecgonine were synthesized by acid catalytic esterification.
publishDate 2024
dc.date.none.fl_str_mv 2024-06-19T12:49:20Z
2024-06-19T12:49:20Z
2024-03-01
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
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dc.identifier.uri.fl_str_mv http://repositorio.ufes.br/handle/10/17397
url http://repositorio.ufes.br/handle/10/17397
dc.language.iso.fl_str_mv por
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dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.format.none.fl_str_mv Text
application/pdf
dc.publisher.none.fl_str_mv Universidade Federal do Espírito Santo
BR
Mestrado em Química
Centro de Ciências Exatas
UFES
Programa de Pós-Graduação em Química
publisher.none.fl_str_mv Universidade Federal do Espírito Santo
BR
Mestrado em Química
Centro de Ciências Exatas
UFES
Programa de Pós-Graduação em Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)
instname:Universidade Federal do Espírito Santo (UFES)
instacron:UFES
instname_str Universidade Federal do Espírito Santo (UFES)
instacron_str UFES
institution UFES
reponame_str Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)
collection Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)
repository.name.fl_str_mv Repositório Institucional da Universidade Federal do Espírito Santo (riUfes) - Universidade Federal do Espírito Santo (UFES)
repository.mail.fl_str_mv
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