1H-NMR study of unheated and heated marijuana and hashish extracts from cannabis seizures in Egypt

  • Alaa El-Din Gaafar National Research Centre, Cairo, Egypt
  • Omar Abdel -Salam National Research Centre, Cairo, Egypt
  • Shaimaa ElShebiney National Research Centre, Cairo, Egypt
  • Hend Ezzat National Research Centre, Cairo, Egypt
Keywords: Cannabis; Hashish, Marijuana, Nuclear Magnetic Resonance

Abstract

: Is to detect the presence of delta-9-tertrahydrocannabinol (THC) and other cannabinoids in samples of cannabis seized in Egypt with the use of nuclear magnetic resonance (1H-NMR). Methods: Extracts of cannabis seizures were prepared from marijuana (the dried flowering tops and leaves) or from hashish (the compressed plant resin). Cannabis extraction was carried out on unheated or heated samples using either chloroform or methanol. 1H-NMR spectrum for cannabis extract was determined in CDCl3 with a JEOL ECA-500. Results: 1H-NMR indicate that the extracts of the cannabis samples contain THC as the major constituent. The 1H-NMR of heated cannabis extracts showed only THC while the 1H-NMR spectra of unheated extracts showed the presence of THC as a major compound beside minor fraction of cannabinol (CBN), both are decraboxylated. Conclusion: The 1H-NMR spectra indicate the presence of THC as the major compound.

Author Biographies

Alaa El-Din Gaafar, National Research Centre, Cairo, Egypt

Department of Photochemistry, National Research Centre, Cairo, Egypt

Omar Abdel -Salam, National Research Centre, Cairo, Egypt

Department of Toxicology and Narcotics, National Research Centre, Cairo, Egypt

Shaimaa ElShebiney, National Research Centre, Cairo, Egypt

Department of Toxicology and Narcotics, National Research Centre, Cairo, Egypt

Hend Ezzat, National Research Centre, Cairo, Egypt

Department of Spectroscopy, National Research Centre, Cairo, Egypt

References

United Nations Office on Drugs and Crime (UNODC). World Drug Report. Vienna, Austria: United Nations Publications (Sales No. E.16.XI.7) (2016).

Ashton C.H., Pharmacology and effects of cannabis: a brief review. British Journal of Psychiatry, 178, 101–106 (2001).

Cole M.D. Cannabis sativa and Products. In: The Analysis of Controlled Substances, John Wiley & Sons, Ltd., p 49-72 (2003).

Huestis M.A. Cannabis (marijuana)—effects on human behavior and performance. Forensic Science Review 14,15 (2002).

Broyd S.J., van Hell H.H., Beale C., Yücel M., and Solowij N. Acute and chronic effects of cannabinoids on human cognition-A systematic review. Biological Psychiatry, 79(7), 557-67 (2016).

Kowal M.A., Hazekamp A., Colzato L.S., van Steenbergen H., van der Wee N.J.A., Durieux J., Manai M., and Hommel B. Cannabis and creativity: highly potent cannabis impairs divergent thinking in regular cannabis users. Psychopharmacology, 232, 1123-1134 (2015).

Pardini D., White H.R., Xiong S., Bechtold J., Chung T., Loeber R., and Hipwell A. Unfazed or dazed and confused: does early adolescent marijuana use cause sustained impairments in attention and academic functioning? Journal of Abnormal Child Psychology, 43(7), 1203-1207 (2015).

Cerdá M., Moffitt T.E., Meier M.H., Harrington H.L., Houts R., Ramrakha S., Hogan S., Poulton R., and Caspi A. Persistent cannabis dependence and alcohol dependence represent risks for midlife economic and social problems: a longitudinal cohort study. Clinical Psychological Science, 4(6), 1028-1046 (2016).

D'Souza D.C., Radhakrishnan R., Sherif M., Cortes-Briones J., Cahill J., Gupta S., Skosnik P.D., and Ranganathan M. Cannabinoids and psychosis. Current Pharmaceutical Design, 22(42), 6380-6391 (2016).

Brenneisen R. Chemistry and analysis of phytocannabinoids and other cannabis constituents. In: ElSohly MA (ed). Forensic Science and Medicine: Marijuana and the Cannabinoids. Totowa, NJ: Humana Press Inc., p.17-49 (2006).

Morales P., Hurst D.P., and Reggio P.H. Molecular targets of the phytocannabinoids-A complex picture. Progress in the Chemistry of Organic Natural Products, 103, 103–131 (2017).

ElSohly M.A., Radwan M.M., Gul W., Chandra S., and Galal A. Phytochemistry of Cannabis sativa L. In: Kinghorn AD, Falk H, Gibbons S, Kobayashi J (eds). Phytocannabinoids Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa. Progress in the Chemistry of Organic Natural Products. Switzerland, Springer International Publishing., p. 1-36 (2017).

Hazekamp A., Tejkalova´ K., and Papadimitriou S. Cannabis: from cultivar to chemovar II—A Metabolomics. Approach to cannabis classification. Cannabis and Cannabinoid Research, 1 (1) (2016).

Gaoni Y., and Mechoulam R. Isolation, structure and partial synthesis of an active constituent of hashish. Journal of the American Chemical Society, 86, 1646-1647 (1964).

Pertwee R. G. The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. British Journal of Pharmacology, 153(2), 199-215 (2008).

Pacifici R., Marchei E., Salvatore F., Guandalini L., Busardò F.P., and Pichini S. Evaluation of cannabinoids concentration and stability in standardized preparations of cannabis tea and cannabis oil by ultra-high performance liquid chromatography tandem mass spectrometry. Clinical Chemistry and Laboratory Medicine, 55(10), 1555-1563 (2017).

Souleman A.M.A., Gaafar AE-D.M., Abdel-Salam O.M., and ElShebiney S.A. Determination of delta-9-tetrahydrocannabinol content of cannabis seizures in Egypt. Asian Pacific Journal of Tropical Medicine, 10 (3), 311-314 (2017).

Hazekamp A., Choi Y.H., and Verpoorte R. Quantitative analysis of cannabinoids from Cannabis sativa using 1H-NMR. Chemical and Pharmaceutical Bulletin, 52(6), 718-721 (2004).

Politi M., Peschel W., Wilson N., Zloh M., Prieto J.M., and Heinrich M. Direct NMR analysis of cannabis water extracts and tinctures and semi-quantitative data on 9-THC and 9-THC-acid. Phytochemistry, 69, 562–570 (2008).

Wang X., Harrington P.B., and Baugh S.F. Comparative study of NMR spectral profiling for the characterization and authentication of cannabis. Journal of AOAC International, 100(5), 1356-1364 (2017).

Fischedick J.T., Glas R., Hazekamp A., and Verpoorte R. A qualitative and quantitative HPTLC densitometry method for the analysis of cannabinoids in Cannabis sativa L. Phytochemical Analysis, 20(5), 421-426 (2009).

Turner J.C., and Mahlberg P.G. Separation of Acid and neutral cannabinoids in Cannabis sativa L. using HPLC. In: Agurell S, Dewey WL, Willete RE (Eds.), Chemical Pharmacol Ther Agents. Academic Press; USA, p.79-88 (1985).

Forseth R.R., and Schroeder F.C. NMR-spectroscopic analysis of mixtures: from structure to function. Current Opinion in Chemical Biology, 15(1): 38–47 (2011).

Dagnino D., and Schripsema J. 1H NMR quantification in very dilute toxin solutions: application to anatoxin-a analysis. Toxicon, 46(2), 236-240 (2005).

Moco S., Bino R.J., De Vos R.C.H., and Vervoort J. Metabolomics technologies and metabolite identification. Trends in Analytical Chemistry 2007; 26 (9): 855-866.

Peschel W. Quality control of traditional cannabis tinctures: pattern, markers, and stability. Scientia Pharmaceutica, 84(3), 567-584 (2016).

United Nations Office on Drugs and Crime (UNODC). Recommended methods for the identification and analysis of cannabis and cannabis products. Vienna, Austria: United Nations Publications, (Sales No. E.09.XI.15)( 2009).

Published
2018-08-29
Section
Research Articles