Synthetic Access to Cannabidiol and Analogs as Active Pharmaceutical Ingredients
Miniperspective
- Michael C. Pirrung*Michael C. Pirrung*Email: [email protected]. Phone: +1 (951) 827-2722.Department of Chemistry, University of California, Riverside, California 92521, United StatesDepartment of Pharmaceutical Sciences, University of California, Irvine, California 92697, United StatesMore by Michael C. Pirrung
Abstract

Cannabinoids have surely been one of the most widely self-administered drugs other than caffeine. The U.S. FDA recently approved one cannabinoid-based drug whose active pharmaceutical ingredient (API) is cannabidiol (CBD). The long history of individual use of cannabis for a wide range of conditions has sparked great interest in other uses of CBD, in ethical drugs and botanical supplements as well as in foods and nonprescription wellness products. CBD may be sourced from cannabis plants but can also be prepared synthetically, the topic of this review.
Cited By
This article is cited by 15 publications.
- Alexandra M. Millimaci, Richard V. Trilles, James H. McNeely, Lauren E. Brown, Aaron B. Beeler, John A. Porco, Jr.. Synthesis of Neocannabinoids Using Controlled Friedel–Crafts Reactions. The Journal of Organic Chemistry 2023, 88 (18) , 13135-13141. https://doi.org/10.1021/acs.joc.3c01362
- Hannah V. Stone, Frederick J. Topping, Alberte X. Veiga, Alexandru Pop, Daniel Miles, Dominika Knych, John Warren, Michael S. Loft, Alejandro Montellano López, Alan Silcock, Inderjit S. Mann, Antoine Millet. Diastereoselective and Scalable Synthesis of 6-(S)-Hydroxycannabidivarin. The Journal of Organic Chemistry 2023, 88 (16) , 11767-11777. https://doi.org/10.1021/acs.joc.3c01057
- Ridhdhi Dave, Gurpreet Randhawa, Daeun Kim, Madeline Simpson, Todd Hoare. Microgels and Nanogels for the Delivery of Poorly Water-Soluble Drugs. Molecular Pharmaceutics 2022, 19 (6) , 1704-1721. https://doi.org/10.1021/acs.molpharmaceut.1c00967
- Alon R. Agua, Philip J. Barr, Charles K. Marlowe, Michael C. Pirrung. Cannabichromene Racemization and Absolute Stereochemistry Based on a Cannabicyclol Analog. The Journal of Organic Chemistry 2021, 86 (12) , 8036-8040. https://doi.org/10.1021/acs.joc.1c00451
- Xiuli Wang, Huanbang Zhang, Yan Liu, Yang Xu, Bingyou Yang, Hua Li, Lixia Chen. An overview on synthetic and biological activities of cannabidiol (CBD) and its derivatives. Bioorganic Chemistry 2023, 140 , 106810. https://doi.org/10.1016/j.bioorg.2023.106810
- Eleana Lopušanskaja, Anne Paju, Ivar Järving, Margus Lopp. A direct alkylation of resorcinols. Synthetic Communications 2023, 53 (15) , 1216-1226. https://doi.org/10.1080/00397911.2023.2214645
- Guanghui Tang, Ying‐Jie Lim, Wei Wang, Zi Ye, Chong‐Jing Zhang, Shao Q. Yao. Orthogonal Strategies for Profiling Potential Cellular Targets of Anandamide and Cannabidiol. Chemistry – A European Journal 2023, 29 (43) https://doi.org/10.1002/chem.202300682
- Beatriz P. Ferreira, Gustavo Costa, Filipa Mascarenhas-Melo, Patrícia C. Pires, Fariba Heidarizadeh, Prabhanjan S. Giram, Priscila Gava Mazzola, Célia Cabral, Francisco Veiga, Ana Cláudia Paiva-Santos. Skin applications of cannabidiol: sources, effects, delivery systems, marketed formulations and safety. Phytochemistry Reviews 2023, 22 (3) , 781-828. https://doi.org/10.1007/s11101-023-09860-5
- Mackenzie M. Aychman, David L. Goldman, Joshua S. Kaplan. Cannabidiol's neuroprotective properties and potential treatment of traumatic brain injuries. Frontiers in Neurology 2023, 14 https://doi.org/10.3389/fneur.2023.1087011
- Susan Miller, Walter Moos, Barbara Munk, Stephen Munk, Charles Hart, David Spellmeyer. Backgrounder—Part 2. 2023, 27-64. https://doi.org/10.1016/B978-0-12-824304-6.00010-9
- Dorota Chelminiak-Dudkiewicz, Aleksander Smolarkiewicz-Wyczachowski, Kinga Mylkie, Magdalena Wujak, Dariusz T. Mlynarczyk, Pawel Nowak, Szymon Bocian, Tomasz Goslinski, Marta Ziegler-Borowska. Chitosan-based films with cannabis oil as a base material for wound dressing application. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-23506-0
- Alice Maiocchi, Jacopo Barbieri, Valerio Fasano, Daniele Passarella. Stereoselective Synthetic Strategies to (−)‐Cannabidiol. ChemistrySelect 2022, 7 (28) https://doi.org/10.1002/slct.202202400
- Zi-Yi Huang, Min-Ru Jiao, Xiu Gu, Zi-Ran Zhai, Jian-Qi Li, Qing-Wei Zhang. Asymmetric Synthesis of 1,2-Limonene Epoxides by Jacobsen Epoxidation. Pharmaceutical Fronts 2021, 03 (03) , e113-e118. https://doi.org/10.1055/s-0041-1740241
- Anderson R. Aguillón, Raquel A. C. Leão, Leandro S. M. Miranda, Rodrigo O. M. A. de Souza. Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes. Chemistry – A European Journal 2021, 27 (18) , 5577-5600. https://doi.org/10.1002/chem.202002887
- Alexandra E. Golliher, Antonio J. Tenorio, Nina O. Dimauro, Nicolas R. Mairata, F. Omar Holguin, William Maio. Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV. Tetrahedron Letters 2021, 67 , 152891. https://doi.org/10.1016/j.tetlet.2021.152891