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Metabolites
Volume 14
Issue 6
10.3390/metabo14060329
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Article

Identification and Characterization of Cannabichromene’s Major Metabolite Following Incubation with Human Liver Microsomes

by
Alexandra M. Ward
1,
Touraj Shokati
2,
Jost Klawitter
2,
Jelena Klawitter
2,
Vu Nguyen
1,
Laura Kozell
3,4,5,
Atheir I. Abbas
3,4,5,
David Jones
6 and
Uwe Christians
2,*
1
Department of Pharmaceutical Sciences, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of Colorado Anschutz Medical Campus, Aurora, CO 80045, USA
2
iC42 Clinical Research and Development, Department of Anesthesiology, School of Medicine, University of Colorado Anschutz Medical Campus, Aurora, CO 80045, USA
3
Department of Behavioral Neuroscience, Oregon Health & Science University, Portland, OR 97239, USA
4
Department of Psychiatry, Oregon Health & Science University, Portland, OR 97239, USA
5
Veterans Affairs Portland Health Care System, Portland, OR 97239, USA
6
Department of Pharmacology, School of Medicine, University of Colorado Anschutz Medical Campus, Aurora, CO 80045, USA
*
Author to whom correspondence should be addressed.
Metabolites 2024, 14(6), 329; https://doi.org/10.3390/metabo14060329
Submission received: 10 May 2024 / Revised: 1 June 2024 / Accepted: 11 June 2024 / Published: 13 June 2024
(This article belongs to the Special Issue Drug Metabolism: Latest Advances and Prospects)
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Abstract

Cannabichromene (CBC) is a minor cannabinoid within the array of over 120 cannabinoids identified in the Cannabis sativa plant. While CBC does not comprise a significant portion of whole plant material, it is available to the public in a purified and highly concentrated form. As minor cannabinoids become more popular due to their potential therapeutic properties, it becomes crucial to elucidate their metabolism in humans. Therefore, the goal of this was study to identify the major CBC phase I-oxidized metabolite generated in vitro following incubation with human liver microsomes. The novel metabolite structure was identified as 2′-hydroxycannabicitran using gas chromatography–mass spectrometry and nuclear magnetic resonance spectroscopy. Following the identification, in silico molecular modeling experiments were conducted and predicted 2′-hydroxycannabicitran to fit in the orthosteric site of both the CB1 and CB2 receptors. When tested in vitro utilizing a competitive binding assay, the metabolite did not show significant binding to either the CB1 or CB2 receptors. Further work necessitates the determination of potential activity of CBC and the here-identified phase I metabolite in other non-cannabinoid receptors.
Keywords: cannabichromene; 2′-hydroxycannabicitran; cannabicitran; human drug metabolism; phase I metabolism; human liver microsomes; gas chromatography–mass spectrometry; nuclear magnetic resonance spectroscopy; molecular docking; CB1 receptor; CB2 receptor; binding cannabichromene; 2′-hydroxycannabicitran; cannabicitran; human drug metabolism; phase I metabolism; human liver microsomes; gas chromatography–mass spectrometry; nuclear magnetic resonance spectroscopy; molecular docking; CB1 receptor; CB2 receptor; binding

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MDPI and ACS Style

Ward, A.M.; Shokati, T.; Klawitter, J.; Klawitter, J.; Nguyen, V.; Kozell, L.; Abbas, A.I.; Jones, D.; Christians, U. Identification and Characterization of Cannabichromene’s Major Metabolite Following Incubation with Human Liver Microsomes. Metabolites 2024, 14, 329. https://doi.org/10.3390/metabo14060329

AMA Style

Ward AM, Shokati T, Klawitter J, Klawitter J, Nguyen V, Kozell L, Abbas AI, Jones D, Christians U. Identification and Characterization of Cannabichromene’s Major Metabolite Following Incubation with Human Liver Microsomes. Metabolites. 2024; 14(6):329. https://doi.org/10.3390/metabo14060329

Chicago/Turabian Style

Ward, Alexandra M., Touraj Shokati, Jost Klawitter, Jelena Klawitter, Vu Nguyen, Laura Kozell, Atheir I. Abbas, David Jones, and Uwe Christians. 2024. "Identification and Characterization of Cannabichromene’s Major Metabolite Following Incubation with Human Liver Microsomes" Metabolites 14, no. 6: 329. https://doi.org/10.3390/metabo14060329

APA Style

Ward, A. M., Shokati, T., Klawitter, J., Klawitter, J., Nguyen, V., Kozell, L., Abbas, A. I., Jones, D., & Christians, U. (2024). Identification and Characterization of Cannabichromene’s Major Metabolite Following Incubation with Human Liver Microsomes. Metabolites, 14(6), 329. https://doi.org/10.3390/metabo14060329

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