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Análise de canabinóides neutros em derivados de Cannabis via GC/MS

Grijó, D. R. ; Cardozo, L. F. ;

Artigo Completo:

Atualmente a medicina tem grande interesse na espécie Cannabis sativa L., especialmente em dois de seus canabinóides neutros (CN): canabidiol (CBD) e 9-tetrahidrocanabinol (9-THC). Em parceria com a Polícia Científica de Curitiba – Brasil, foram feitas análises, via cromatografia gasosa e espectrometria de massas (GC/MS), da composição e o comportamento térmico de CN em derivados dessa espécie, com solvente polar e apolar. Testou-se também, em sementes, uma metodologia industrial de limpeza para remover resíduos de CN aderidos por contato com outras partes da planta. A partir de curvas de calibração, utilizando padrões de CBD, 9-THC e canabinol (CBN), foi possível fazer análises quantitativas da influência térmica e da metodologia de lavagem. Esses e outros canabinóides foram identificados pela razão massa carga (m/z). Foi comprovado que o aquecimento de amostras aumenta o potencial medicinal, mas também transforma o 9-THC em CBN e/ou 8-tetraidrocanabinol (8-THC), e o CBD em canabielsoin (CBE) e/ou 9-THC. O extrato apolar apresentou maior concentração de CN. Demonstrou-se também a diminuição de CN nas sementes pelo método de lavagem industrial, bem como o rendimento em óleo esperado em referências. Com esse trabalho foi possível demonstrar a importância de conhecimento do comportamento dos CN em derivados de Cannabis.

Artigo Completo:

Currently the medicine has great interest in the species Cannabis sativa L., especially in two of its neutral cannabinoids (CN): cannabidiol (CBD) and 9-tetrahydrocanabinol (9-THC). In partnership with the Scientific Policy of Curitiba - Brazil, analyses had been made, with gas chromatography and mass spectrometry (GC/MS), of the composition and the thermal behavior of CN in derivatives of this species, with polar and nonpolar solvent. It was also tested in seeds an industrial cleaning method to remove CN residues adhered by contact with other parts of the plant. From the calibration curves using the standards CBD, 9-THC and canabinol (CBN), it was possible to make quantitative analysis of the thermal influence and the cleaning method. Those and others canabinnoids were identified by mass/charge ratio (m/z). It was proven that the heating samples increases the medicinal potential, but also transforms 9-THC in CBN and/or 8-tetraidrocanabinol (8-THC), and CBD in canabielsoin (CBE) and/or 9-THC. The nonpolar extract has a higher concentration of CN. Cleaning method reduce CN in seeds, as well oil yield expected results. With this work it was possible to demonstrate the importance of knowledge of the CN behavior in Cannabis derivatives.

Palavras-chave: cannabinoids, gas chromatography, mass spectrometry.,

Palavras-chave: ,

DOI: 10.5151/SEQUFES2016-006

Referências bibliográficas
  • [1] ANVISA. Agência Nacional de Vigilância Sanitária. Resolução – RDC Nº 87, de 28 de Junho, 2016.
  • [2] NIST. National Institute of Standards and Technology. Material Measurement Laboratory. Web book, 2016.
  • [3] MECHOULAM, R., GAONI, Y. Recent advances in the chemistry of hashish. Fortschr, Chem. Org. Naturst. 25, 175-213, 1967.
  • [4] FASSIO, A. et al. Cáñamo (Cannabis sativa L.). Instituto Nacional de Investigación Agropecuária INIA – Uruguay. Noviembre, 2013.
  • [5] TURNER, C. E. et al. Constituents of Cannabis sativa L.. J. Nat. Prod. 43, 169-234, 1980.
  • [6] HEMP MEDS. California. United States. 2016
  • [7] BLUE BIRD BOTANICALS. Colorado. United States. 2016
  • [8] ENDOCA. Copenhagen. Denmark. 2016.
  • [9] BREDOCAN. Veendam. Nertherland. 2016.
  • [10] BRUNEL, H. Sustainable Production of Cannabinoids with Supercritical Carbon Dioxide Technologies Grade de Master en Génie Chimique, Université de Technologie de Compiègne. 2011.
  • [11] ALADIĆ, K. et al. Supercritical CO2 extraction of hemp (Cannabis sativa L.) seed oil. Industrial Crops and Products 76 472–478, 2015.
  • [12] SALAM A. Effect of Cannabis sativa extract on gastric acid secretion, oxidative stress and gastric mucosal integrity in rats. Comparative Clinical Pathology, Vol.24(6), pp.1417-1434, 2015.
  • [13] KIRALAM, M., et al. Fatty acid composition of hempseed oils from different locations in Turkey. Instituto Nacional de Investigación y Tecnología Agraria y Alimentaria (INIA). Spanish Journal of Agricultural Research 8(2), 385-390, 2010.
  • [14] STAMBOULI, H.; et al. Cultivation of Cannabs sativa L. in northern Morocco. Bulletin on Narcotics, vol. LVII, Nos, 1 and 2, 2005.
  • [15] TASCHWER, M.; SCHMID, M. G. Determination of the relative percentage distribution of THCA and Δ9-THC in herbal Cannabis seized in Austria – Impact of different storage temperatures on stability. Forensic Science International 254 167–171, 20
  • [16] VERESS T., et al. Determination of cannabinoid acids by high-performance liquid chromatography of their neutral derivatives formed by thermal decarboxylation in an open re-actor. J. Chromatogr. 520: 339-347, 1990.
  • [17] GARRET, E. R. Stability of Tetrahydrocannabinols I. College of Pharmacy. University of Florida, 1974.
  • [18] SHANI, A.; MECHOULAM, R. Cannabielsoic acids. Isolation and synthesis by a novel oxidative cyclization. Tetraedron, v30, issue 15, pages 2437-2446, 1974.
  • [19] RUSSO, E. B.; et al. Phytochemical and genetic analyses of ancient Cannabis from Central Asia. J Exp Botany, Vol. 59, Nº. 15, pp. 4171–4182, 2008.
  • [20] ADAMS, R. et al. Isomerization of Cannabidiol to Tetrahydrocannabinol, a Physiologically Active Product. Conversion of Cannabidiol to Cannabinol. J of the American Chem Soc, v62 iss:9 2402 -2405, 1940.
  • [21] UNODC. United Nations Office on Drugs and Crime. Recommended methods for the identification and analysis of Cannabis and Cannabis products, 2009.
  • [22] RYMANOWSKI, M. Cannabis – review of the issues related to determination of the total content of 9-THC and 9-THCA-A. Problemy KryminalistykI 285(3), 2014
  • [23] BRENNEISEN R. Chemistry and analysis of phytocannabinoids and other Cannabis constituents. Edited by: M. A. ElSohly Humana Press Inc, 2007.
  • [24] LACHENMEIER, D.W. et al. Determination of cannabinoids in hemp food products by use of headspace solid-phase microextraction and gas chromatography–mass spectrometry. Anal Bioanal Chem 378 : 183–189, 2004.
  • [25] MEDIAVILLA, V. et al. Qualität von Hanfsamenöl aus der Schweiz. Agrarforschung 4, 449–451, 1997.
  • [26] LESON, G. et al. Evaluating the impact of hemp food consumption on workplace drug tests. J. Anal. Toxicol. 25, 691–698, 2001.
  • [27] ELSOHLY, M. A. Practical challenges to positive drug tests for marijuana. ClinChem49 1037:1038, 2003.
  • [28] MAASI. Manitoba Association of Agricultural Societies Inc. Development of Hemp Food Products & Processes, 2000.
  • [29] LINK, D. J. Fundamentos e estratégias para comercialização de soja e milho e produção de sementes de soja. CCA/UFSC, 2011.
  • [30] GRIJÓ, D. R., MELO, B. N. “Análise Potencial de Ácidos Graxos Poli-insaturados em Sementes de Cânhamo. Biomassa BR, ed 25, p 30, 2016. Disponível Acessado em: 23 Set, 2016
  • [31] Government of Canada. Governments Invest in Bringing Made-in-Manitoba Foods to Market. Disponível . Acesso em: 22 Set, 2016.
  • [32] LI, S. Y. et al. The feasibility of converting Cannabis oil into biodiesel, BioRTech 101 (21) : 8457-60, 2010.
  • [33] VOLG, C. R. et al. Hemp as a resource for green cosmetics: yield of seed and fatty acid composition of 20 varieties under the growing conditions of organic farming in Austria. J Ind Hemp 9(1), 51-68, 2004.
  • [34] SURENDER, R. et al. Synthesis, characterization and degradation behavior of thermoplastic polyurethane from hydroxylated hemp seed oil. Journal of Thermal Analysis and Calorimetry, 2016.
  • [35] BgVV. German Federal Institute for Consumer Health Protection and Veterinary Medicine. Einsatz von Hanf in Lebensmitteln kann gesundheitlich problematisch sein. BgVV Pressedienst, Berlin, Germany, 1997.
Como citar:

Grijó, D. R.; Cardozo, L. F.; "Análise de canabinóides neutros em derivados de Cannabis via GC/MS", p. 23-27 . In: . São Paulo: Blucher, 2017.
ISSN 2359-1757, DOI 10.5151/SEQUFES2016-006

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