Аналіз канабісу та його продуктів у контексті судової експертизи
DOI:
https://doi.org/10.32353/khrife.1.2024.06Ключові слова:
канабіс; фітоканабіноїди; екстрагування; ідентифікація; кількісне визначення; газова хроматографія; рідинна хроматографія; метод ядерного магнітного резонансу; методи коливальної спектроскопії.Анотація
Легалізація вирощування рослин роду Cannabis із низьким умістом тетрагідроканабінолу й високим умістом канабідіолу набирає обертів через зростання попиту на ці продукти. У деяких країнах тестування канабісу та продуктів, що його містять, є юридичною вимогою: канабіс ідентифікують, оцінюють кількість у ньому тетрагідроканабінолу або канабідіолу та їхніх кислот-попередниць. Сучасні дослідження потребують більш чутливих і надійних аналітичних методів для точної ідентифікації та кількісного визначення компонентів канабісу. Мета цієї статті — огляд представлених у наукових джерелах останніх досягнень щодо виокремлення й аналізу канабісу та продуктів, які його містять, у контексті судової експертизи. Методи дослідження містили аналіз інформації із цієї тематики за допомогою пошукових систем, зокрема Google, Google Scholar, Web of Science, PubMed і ScienceDirect. Пошукові запити враховували наукові, аналітичні та статистичні звіти в галузі судово-експертних досліджень. Оскільки судовий експерт має добре орієнтуватися в сучасних тенденціях аналізу заборонених речовин і послуговуватися у своїй роботі останніми даними аналітичної та судово-криміналістичної літератури, така інформація допоможе їм обирати методи проведення досліджень, зважаючи на фактичні ресурси й обладнання судово-криміналістичних лабораторій. Згідно з метою статті розглянуто переваги і недоліки наявних методів екстрагування й аналізу об’єктів, що містять канабіс, для ідентифікації, кількісного визначення, профілювання та оцінювання віку канабісу.
Посилання
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Borges, G. R., Birk, L., Scheid, C., Morés, L., Carasek, E., Kitamura, R. O. S., Roveri, F. L. et al. (2020). Simple and Straightforward Analysis of Cannabinoids in Medicinal Products by Fast-GC-FID. Forensic Toxicology. Vol. 38. DOI: 10.1007/s11419-020-00522-1.
Brighenti, V., Pellati, F., Steinbach, M., Maran, D., Benvenuti, S. (2017). Development of a New Extraction Technique and HPLC Method for the Analysis of Non-Psychoactive Cannabinoids in Fibre-Type Cannabis Sativa L. (Hemp). Journal of Pharmaceutical and Biomedical Analysis. Vol. 143. DOI: 10.1016/j.jpba.2017.05.049.
Calvi, L., Pentimalli, D., Panseri, S., Giupponi, L., Gelmini, F., Beretta, G., Vitali, D., Bruno, M., Zilio, E., Pavlovic, R., Giorgi, A. (2018). Comprehensive Quality Evaluation of Medical Cannabis Sativa L. Inflorescence and Macerated Oils Based on HS-SPME Coupled to GC-MS and LC-HRMS (q-exactive Оrbitrap®) Approach. Journal of Pharmaceutical and Biomedical Analysis. Vol. 150. DOI: 10.1016/j.jpba.2017.11.073.
Cardenia, V., Toschi, T. G., Scappini, S., Rubino, R. C., Rodriguez-Estrada, M. T. (2018). Development and Validation of a Fast Gas Chromatography/Mass Spectrometry Method for the Determination of Cannabinoids in Cannabis Sativa L. Journal of Food and Drug Analysis. Vol. 26 (4). DOI: 10.1016/j.jfda.2018.06.001.
CBOL Plant Working Group, Hollings-worth, P. M., Forrest, L. L., Little, D. P. (2009). A DNA Barcode for Land Plants. Proceedings of the National Academy of Sciences USA. Vol. 106. Is. 31. DOI: 10.1073/ pnas.0905845106.
Chang, Ch.-W., Tung, Ch.-W., Tsai, Ch.-Ch., Wu, Yu-T., Hsu, M.-Ch. (2017). Determination of Cannabinoids in Hemp Nut Products in Taiwan by HPLC-MS/MS Coupled with Chemometric Analysis: Quality Evaluation and a Pilot Human Study. Drug Testing and Analysis. No. 9. DOI: 10.1002/dta.2062.
Christinat, N., Savoy, M.-C., Mottier, P. (2020). Development, Validation and Application of a LC-MS/MS Method for Quantification of 15 Cannabinoids in Food. Food Chemistry. Vol. 318. Art. 126469. DOI: 10.1016/j. foodchem.2020.126469.
Ciolino, L. A., Ranieri, T. L., Taylor, A. M. (2018). Commercial cannabis consumer products part 1: GC-MS qualitative analysis of cannabis cannabinoids. Forensic Science International. Vol. 289. DOI: 10.1016/j. forsciint.2018.05.032.
Citti, C., Russo, F., Sgrò, S., Gallo, A., Zanotto, A., Forni, F., Vandelli, M. A., Laganà, A., Montone, C. M., Gigli, G., Cannazza, G. (2020). Pitfalls in the analysis of phytocannabinoids in cannabis inflorescence. Analytical and Bioanalytical Chemistry. Vol. 412. No. 17. Art. 4009—4022. DOI: 10.1007/s00216-020-02554-3.
Cuttler, C., LaFrance, E. M., Stueber, A. (2021). Acute effects of high-potency cannabis flower and cannabis concentrates on everyday life memory and decision making. Scientific Reports. Vol. 11. No. 1. Art. 13784. DOI: 10.1038/s41598-021-93198-5.
De Leite, J. A., de Oliveira, M. V. L., Conti, R., de S. Borges, W., Rosa, Th. R., Filguei-ras, P. R., Lacerda, Jr. V., Romão, W., Neto, Á. C. (2018). Extraction and isolation of cannabinoids from marijuana seizures and characterization by 1H NMR allied to chemometric tools. Science & Justice. Vol. 58. Is. 5. DOI: 10.1016/j.scijus.2018.06.005.
De Vita, D., Madia, V. N., Tudino, V., Saccoliti, F., De Leo, A., Messore, A., Roscilli, P., Botto, A., Pindinello, I., Santilli, G. et al. (2019). Comparison of Different Methods for the Extraction of Cannabinoids from Cannabis. Natural Product Research. Vol. 34 (20). DOI: 10.1080/14786419.2019.1601194.
Deidda, R., Dispas, A., De Bleye, Ch., Hubert, Ph., Ziemons, É. (2021). Critical review on recent trends in cannabinoid determination on cannabis herbal samples: From chromatographic to vibrational spectroscopic techniques. Analytica Chimica Acta. May 29:1209:339184. DOI: 10.1016/j. aca.2021.339184.
Delgado-Povedano, M. M., Sánchez-Carnerero Callado, C., Priego-Capote, F., Ferreiro-Vera, C. (2020). Untargeted Characterization of Extracts from Cannabis Sativa L. Cul-tivars by Gas and Liquid Chromatography Coupled to Mass Spectrometry in High Resolution Mode. Talanta. Vol. 208. Art. 120384. DOI: 10.1016/j.talanta.2019.120384.
Deville, M., Dubois, N., Denooz, R., Charlier, C. (2020). Validation of an UHPLC/DAD Method for the Determination of Cannabinoids in Seized Materials: Analysis of 213 Samples Sold in Belgian CBD shops. Forensic Science International. Vol. 310. Art. 110234. DOI: 10.1016/j.forsciint.2020.110234.
Duchateau, C., Kauffmann, J.-M., Canfyn, M., Stévigny, C., De Braekeleer, K., Deconinck, E. (2020). Discrimination of legal and illegal Cannabis spp. according to European legislation using near infrared spectroscopy and chemometrics. Drug Testing and Analysis. Vol. 12. No. 9. DOI: 10.1002/dta.2865.
ElSohly, M. A., Chandra, S., Radwan, M., Majumdar, Ch. G., Church, J. C. (2021). A Comprehensive Review of Cannabis Potency in the United States in the Last Decade. Biological Psychiatry: Cognitive Neuroscience and Neuroimaging. Vol. 6. No. 6. DOI: 10.1016/j.bpsc.2020.12.016.
European Drug Report 2023: Trends and Developments (2023). Lisbon : EMCDDA. URL: https://www.emcdda. europa.eu/ index_en.
Mandrioli, M., Tura, M., Scotti, S., Toschi, T. G. (2019). Fast Detection of 10 Сannabinoids by RP-HPLC-UV Method in Cannabis sativa L. Molecules. Is. 24. No. 11. Art. 2113. DOI: 10.3390/molecules24112113.
Mariottі, K. C., Marcelo, M. C. A., Ortiz, R. S., Borille, B. T., dos Reis, M., Fett, M. S., Ferrão, M. F., Limberger, R. P. (2016). Seized Cannabis Seeds Cultivated in Greenhouse: A Chemical Study by Gas Hromatography-Mass Spectrometry and Chemometric Analysis. Science & Justice. Vol. 56. DOI: 10.1016/j.scijus.2015.09.002.
McRae, G., Melanson, J. E. (2020). Quantitative Determination and Validation of 17 Canna-binoids in Cannabis and Hemp Using Liquid Chromatography-Tandem Mass Spectrome-try. Analytical and Bioanalytical Chemistry. Vol. 412. No. 27. DOI: 10.1007/s00216-020-02862-8.
Micalizzi, G., Vento, F., Alibrando, F., Donnarum-ma, D., Dugo, P., Mondello, L. (2021). Canna-bis Sativa L.: A comprehensive review on the analytical methodologies for cannabinoids and terpenes characterization. Journal of Chromatography A. Jan 25:1637:461864. DOI: 10.1016/j.chroma.2020.461864.
Mudge, E. M., Murch, S. J., Brown, P. N. (2017). Leaner and Greener Analysis of Cannabinoids. Analytical and Bioanalytical Chemistry. Vol. 409. DOI: 10.1007/s00216-017-0256-3.
Recommended methods for the identification and analysis of Cannabis and Cannabis products (2022) / United Nations Office on Drugs and Crime. March 2022. URL: h t t p s : // w w w.u n o d c .o r g / u n o d c /e n / scientists/recommended-methods-for-the-identification-and-analysis-of-cannabis-and-cannabis-products.html.
Rovetto, L. J., Aieta, N. V. (2017). Supercritical Carbon Dioxide Extraction of Cannabinoids from Cannabis Sativa L. The Journal of Supercritical Fluids. Vol. 129. DOI: 10.1016/j. supflu.2017.03.014.
Sanchez, L., Filter, C., Baltensperger, D., Kurouski, D. (2020). Confirmatory non-invasive and non-destructive differentiation between hemp and cannabis using a hand-held Raman spectrometer. Royal Society of Chemistry Advances. Vol. 10. Is. 6. DOI: 10.1039/C9RA08225E.
Sánchez-Carnerero Callado, C., Núñez-Sánchez, N., Casano, S., Ferreiro-Vera, C. (2018). The potential of near infrared spectroscopy to estimate the content of cannabinoids in Cannabis sativa L.: A comparative study. Talanta. Vol. 90. No. 1. DOI: 10.1016/j. talanta.2018.07.085.
Sgrò, S., Lavezzi, B., Caprari, C., Polito, M., D’Elia, M., Lago, G., Furlan, G., Girotti, S., Ferri, E. N. (2021). Delta9-THC Determination by the EU Official Method: Evaluation of Measurement Uncertainty and Compliance Assessment of Hemp Samples. Analytical and Bioanalytical Chemistry. Vol. 413. No. 13. DOI: 10.1007/s00216-021-03283-x.
Slosse, A., Van Durme, F., Samyn, N., Mangelings, D., Vander Heyden, Yv. (2021). Gas Chromatographic Fingerprint Analysis for the Comparison of Seized Сannabis Samples. Molecules. Vol. 26. Is. 21. Art. 6643. DOI: 10.3390/molecules26216643.
Stefkov, G., Cvetkovikj Karanfilova, I., Stoilkov-ska Gjorgievska, V., Trajkovska, A., Geskovski, N., Karapandzova, M., Kulevanova, S. (2022). Analytical Techniques for Phytocan-nabinoid Profiling of Cannabis and Canna-bis-Based Products — A Comprehensive Re-view. Molecules. Vol. 27. Is. 3. Art. 975. DOI: 10.3390/molecules27030975.
Valizadehderakhshan, M., Shahbazi, A., Kazem-Rostami, M., Todd, M. S., Bhowmik, A., Wang, L. (2021). Extraction of Cannabinoids from Cannabis sativa L. (Hemp) — Review. Agriculture. Vol. 11. Is. 5. Art. 384. DOI: 10.3390/agriculture11050384.
Appley, M. G., Chambers, M. I., Musah, R. A. (2021). Quantification of Hordenine in a Complex Plant Matrix by Direct Analysis in Real Time-High-Resolution Mass Spectrometry: Application to the “Plant of Concern” Sceletium Tortuosum. Drug Testing and Analysis. Vol. 14. Is. 4. DOI: 10.1002/dta.3193.
Borges, G. R., Birk, L., Scheid, C., Morés, L., Carasek, E., Kitamura, R. O. S., Roveri, F. L. et al. (2020). Simple and Straightforward Analysis of Cannabinoids in Medicinal Products by Fast-GC-FID. Forensic Toxicology. Vol. 38. DOI: 10.1007/s11419-020-00522-1.
Brighenti, V., Pellati, F., Steinbach, M., Maran, D., Benvenuti, S. (2017). Development of a New Extraction Technique and HPLC Method for the Analysis of Non-Psychoactive Cannabinoids in Fibre-Type Cannabis Sativa L. (Hemp). Journal of Pharmaceutical and Biomedical Analysis. Vol. 143. DOI: 10.1016/j.jpba.2017.05.049.
Calvi, L., Pentimalli, D., Panseri, S., Giupponi, L., Gelmini, F., Beretta, G., Vitali, D., Bruno, M., Zilio, E., Pavlovic, R., Giorgi, A. (2018). Comprehensive Quality Evaluation of Medical Cannabis Sativa L. Inflorescence and Macerated Oils Based on HS-SPME Coupled to GC-MS and LC-HRMS (q-exactive Оrbitrap®) Approach. Journal of Pharmaceutical and Biomedical Analysis. Vol. 150. DOI: 10.1016/j.jpba.2017.11.073.
Cardenia, V., Toschi, T. G., Scappini, S., Rubino, R. C., Rodriguez-Estrada, M. T. (2018). Development and Validation of a Fast Gas Chromatography/Mass Spectrometry Method for the Determination of Cannabinoids in Cannabis Sativa L. Journal of Food and Drug Analysis. Vol. 26 (4). DOI: 10.1016/j.jfda.2018.06.001.
CBOL Plant Working Group, Hollings-worth, P. M., Forrest, L. L., Little, D. P. (2009). A DNA Barcode for Land Plants. Proceedings of the National Academy of Sciences USA. Vol. 106. Is. 31. DOI: 10.1073/ pnas.0905845106.
Chang, Ch.-W., Tung, Ch.-W., Tsai, Ch.-Ch., Wu, Yu-T., Hsu, M.-Ch. (2017). Determination of Cannabinoids in Hemp Nut Products in Taiwan by HPLC-MS/MS Coupled with Chemometric Analysis: Quality Evaluation and a Pilot Human Study. Drug Testing and Analysis. No. 9. DOI: 10.1002/dta.2062.
Christinat, N., Savoy, M.-C., Mottier, P. (2020). Development, Validation and Application of a LC-MS/MS Method for Quantification of 15 Cannabinoids in Food. Food Chemistry. Vol. 318. Art. 126469. DOI: 10.1016/j. foodchem.2020.126469.
Ciolino, L. A., Ranieri, T. L., Taylor, A. M. (2018). Commercial cannabis consumer products part 1: GC-MS qualitative analysis of cannabis cannabinoids. Forensic Science International. Vol. 289. DOI: 10.1016/j. forsciint.2018.05.032.
Citti, C., Russo, F., Sgrò, S., Gallo, A., Zanotto, A., Forni, F., Vandelli, M. A., Laganà, A., Montone, C. M., Gigli, G., Cannazza, G. (2020). Pitfalls in the analysis of phytocannabinoids in cannabis inflorescence. Analytical and Bioanalytical Chemistry. Vol. 412. No. 17. Art. 4009—4022. DOI: 10.1007/s00216-020-02554-3.
Cuttler, C., LaFrance, E. M., Stueber, A. (2021). Acute effects of high-potency cannabis flower and cannabis concentrates on everyday life memory and decision making. Scientific Reports. Vol. 11. No. 1. Art. 13784. DOI: 10.1038/s41598-021-93198-5.
De Leite, J. A., de Oliveira, M. V. L., Conti, R., de S. Borges, W., Rosa, Th. R., Filguei-ras, P. R., Lacerda, Jr. V., Romão, W., Neto, Á. C. (2018). Extraction and isolation of cannabinoids from marijuana seizures and characterization by 1H NMR allied to chemometric tools. Science & Justice. Vol. 58. Is. 5. DOI: 10.1016/j.scijus.2018.06.005.
De Vita, D., Madia, V. N., Tudino, V., Saccoliti, F., De Leo, A., Messore, A., Roscilli, P., Botto, A., Pindinello, I., Santilli, G. et al. (2019). Comparison of Different Methods for the Extraction of Cannabinoids from Cannabis. Natural Product Research. Vol. 34 (20). DOI: 10.1080/14786419.2019.1601194.
Deidda, R., Dispas, A., De Bleye, Ch., Hubert, Ph., Ziemons, É. (2021). Critical review on recent trends in cannabinoid determination on cannabis herbal samples: From chromatographic to vibrational spectroscopic techniques. Analytica Chimica Acta. May 29:1209:339184. DOI: 10.1016/j. aca.2021.339184.
Delgado-Povedano, M. M., Sánchez-Carnerero Callado, C., Priego-Capote, F., Ferreiro-Vera, C. (2020). Untargeted Characterization of Extracts from Cannabis Sativa L. Cul-tivars by Gas and Liquid Chromatography Coupled to Mass Spectrometry in High Resolution Mode. Talanta. Vol. 208. Art. 120384. DOI: 10.1016/j.talanta.2019.120384.
Deville, M., Dubois, N., Denooz, R., Charlier, C. (2020). Validation of an UHPLC/DAD Method for the Determination of Cannabinoids in Seized Materials: Analysis of 213 Samples Sold in Belgian CBD shops. Forensic Science International. Vol. 310. Art. 110234. DOI: 10.1016/j.forsciint.2020.110234.
Duchateau, C., Kauffmann, J.-M., Canfyn, M., Stévigny, C., De Braekeleer, K., Deconinck, E. (2020). Discrimination of legal and illegal Cannabis spp. according to European legislation using near infrared spectroscopy and chemometrics. Drug Testing and Analysis. Vol. 12. No. 9. DOI: 10.1002/dta.2865.
ElSohly, M. A., Chandra, S., Radwan, M., Majumdar, Ch. G., Church, J. C. (2021). A Comprehensive Review of Cannabis Potency in the United States in the Last Decade. Biological Psychiatry: Cognitive Neuroscience and Neuroimaging. Vol. 6. No. 6. DOI: 10.1016/j.bpsc.2020.12.016.
European Drug Report 2023: Trends and Developments (2023). Lisbon : EMCDDA. URL: https://www.emcdda. europa.eu/ index_en.
Mandrioli, M., Tura, M., Scotti, S., Toschi, T. G. (2019). Fast Detection of 10 Сannabinoids by RP-HPLC-UV Method in Cannabis sativa L. Molecules. Is. 24. No. 11. Art. 2113. DOI: 10.3390/molecules24112113.
Mariottі, K. C., Marcelo, M. C. A., Ortiz, R. S., Borille, B. T., dos Reis, M., Fett, M. S., Ferrão, M. F., Limberger, R. P. (2016). Seized Cannabis Seeds Cultivated in Greenhouse: A Chemical Study by Gas Hromatography-Mass Spectrometry and Chemometric Analysis. Science & Justice. Vol. 56. DOI: 10.1016/j.scijus.2015.09.002.
McRae, G., Melanson, J. E. (2020). Quantitative Determination and Validation of 17 Canna-binoids in Cannabis and Hemp Using Liquid Chromatography-Tandem Mass Spectrome-try. Analytical and Bioanalytical Chemistry. Vol. 412. No. 27. DOI: 10.1007/s00216-020-02862-8.
Micalizzi, G., Vento, F., Alibrando, F., Donnarum-ma, D., Dugo, P., Mondello, L. (2021). Canna-bis Sativa L.: A comprehensive review on the analytical methodologies for cannabinoids and terpenes characterization. Journal of Chromatography A. Jan 25:1637:461864. DOI: 10.1016/j.chroma.2020.461864.
Mudge, E. M., Murch, S. J., Brown, P. N. (2017). Leaner and Greener Analysis of Cannabinoids. Analytical and Bioanalytical Chemistry. Vol. 409. DOI: 10.1007/s00216-017-0256-3.
Recommended methods for the identification and analysis of Cannabis and Cannabis products (2022) / United Nations Office on Drugs and Crime. March 2022. URL: h t t p s : // w w w.u n o d c .o r g / u n o d c /e n / scientists/recommended-methods-for-the-identification-and-analysis-of-cannabis-and-cannabis-products.html.
Rovetto, L. J., Aieta, N. V. (2017). Supercritical Carbon Dioxide Extraction of Cannabinoids from Cannabis Sativa L. The Journal of Supercritical Fluids. Vol. 129. DOI: 10.1016/j. supflu.2017.03.014.
Sanchez, L., Filter, C., Baltensperger, D., Kurouski, D. (2020). Confirmatory non-invasive and non-destructive differentiation between hemp and cannabis using a hand-held Raman spectrometer. Royal Society of Chemistry Advances. Vol. 10. Is. 6. DOI: 10.1039/C9RA08225E.
Sánchez-Carnerero Callado, C., Núñez-Sánchez, N., Casano, S., Ferreiro-Vera, C. (2018). The potential of near infrared spectroscopy to estimate the content of cannabinoids in Cannabis sativa L.: A comparative study. Talanta. Vol. 90. No. 1. DOI: 10.1016/j. talanta.2018.07.085.
Sgrò, S., Lavezzi, B., Caprari, C., Polito, M., D’Elia, M., Lago, G., Furlan, G., Girotti, S., Ferri, E. N. (2021). Delta9-THC Determination by the EU Official Method: Evaluation of Measurement Uncertainty and Compliance Assessment of Hemp Samples. Analytical and Bioanalytical Chemistry. Vol. 413. No. 13. DOI: 10.1007/s00216-021-03283-x.
Slosse, A., Van Durme, F., Samyn, N., Mangelings, D., Vander Heyden, Yv. (2021). Gas Chromatographic Fingerprint Analysis for the Comparison of Seized Сannabis Samples. Molecules. Vol. 26. Is. 21. Art. 6643. DOI: 10.3390/molecules26216643.
Stefkov, G., Cvetkovikj Karanfilova, I., Stoilkov-ska Gjorgievska, V., Trajkovska, A., Geskovski, N., Karapandzova, M., Kulevanova, S. (2022). Analytical Techniques for Phytocan-nabinoid Profiling of Cannabis and Canna-bis-Based Products — A Comprehensive Re-view. Molecules. Vol. 27. Is. 3. Art. 975. DOI: 10.3390/molecules27030975.
Valizadehderakhshan, M., Shahbazi, A., Kazem-Rostami, M., Todd, M. S., Bhowmik, A., Wang, L. (2021). Extraction of Cannabinoids from Cannabis sativa L. (Hemp) — Review. Agriculture. Vol. 11. Is. 5. Art. 384. DOI: 10.3390/agriculture11050384.
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2024-03-29
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Kuchynska, I. (2024). Аналіз канабісу та його продуктів у контексті судової експертизи. Теорія та практика судової експертизи і криміналістики, 34(1), 92–110. https://doi.org/10.32353/khrife.1.2024.06
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