Síntese Metabólitos da Cocaína e Estudos de Métodos Analíticos a Partir de Drogas Apreendidas
Autor(a) principal: | |
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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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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 |
status_str |
publishedVersion |
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 |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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 |
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Universidade Federal do Espírito Santo (UFES) |
instacron_str |
UFES |
institution |
UFES |
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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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