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Cannabidiol

Not to be confused with cannabinol or cannabinodiol.

Cannabidiol
Clinical data
Trade namesEpidiolex, Epidyolex
Other namesCBD, cannabidiolum, (−)-cannabidiol[1]
AHFS/Drugs.comMonograph
MedlinePlusa618051
License data
Pregnancy
category
Addiction
liability		Low[3]
Routes of
administration		Inhalation (smoking, vaping), buccal (aerosol spray),[4][5] oral (solution)[6][7]
Drug classcannabinoid
ATC code
Legal status
Legal status
  • AU: S3 (Pharmacist only)
  • BR: Synthetic: C3; Oil with <0,2% THC: B1; Oil <30mg/ml THC and <30mg/ml CBD: A3.[10]
  • CA: Unscheduled
  • UK: General sales list (GSL, OTC)[11]
  • US: Unscheduled if derived from hemp with less than 0.3% D9-THC but may be considered Schedule I if a component of marijuana with more than 0.3% D9-THC.[8][9]
  • EU: Rx-only[12]
Pharmacokinetic data
Bioavailability
Elimination half-life18–32 hours[15]
Identifiers
  • 2-[(1R,6R)-6-Isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.215.986 Edit this at Wikidata
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
Melting point66 °C (151 °F)
Solubility in waterInsoluble
  • Oc1c(c(O)cc(c1)CCCCC)[C@@H]2\C=C(/CC[C@H]2\C(=C)C)C
  • InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1{PubChem}
  • Key:QHMBSVQNZZTUGM-ZWKOTPCHSA-N{PubChem}
  (verify)
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Cannabidiol (CBD) (/kæ.nə.bə.ˈdaɪ.əl/) is a phytocannabinoid discovered in 1940. It is one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract.[16] As of 2022, clinical research on CBD included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that cannabidiol is effective for these conditions.[17][18][19][20] CBD is also sold as a herbal dietary supplement promoted with unproven claims of particular therapeutic effects.[21]

Cannabidiol can be taken internally in multiple ways, including by inhaling cannabis smoke or vapor, oral, and as an aerosol spray into the cheek.[4][5] It may be supplied as CBD oil containing only CBD as the active ingredient (excluding THC or terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, or prescription liquid solution.[7][19] CBD does not have the same psychoactivity as THC,[22][23] and can modulate the psychoactive effects of THC on the body if both are present.[16][22][24][25] CBD heated to 250–300 °C may partially be converted into THC.[26]

In the United States, the cannabidiol drug Epidiolex was approved by the Food and Drug Administration (FDA) in 2018 for the treatment of two epilepsy disorders.[7] While the 2018 United States Farm Bill removed hemp and hemp extracts (including CBD) from the Controlled Substances Act, the marketing and sale of CBD formulations for medical use or as an ingredient in dietary supplements or manufactured foods remains illegal under FDA regulation, as of 2024.[27][28]

  1. ^ "cannabidiol (CHEBI:69478)". ebi.ac.uk. Archived from the original on May 12, 2021. Retrieved February 12, 2019.
  2. ^ "Epidyolex". Therapeutic Goods Administration (TGA). September 29, 2020. Archived from the original on October 30, 2021. Retrieved September 30, 2020.
  3. ^ "Schedules of Controlled Substances: Placement in Schedule V of Certain FDA-Approved Drugs Containing Cannabidiol; Corresponding Change to Permit Requirements". Federal Register, US Federal Government. September 28, 2018. Retrieved March 10, 2024.
  4. ^ a b Itin C, Barasch D, Domb AJ, Hoffman A (May 2020). "Prolonged oral transmucosal delivery of highly lipophilic drug cannabidiol". International Journal of Pharmaceutics. 581: 119276. doi:10.1016/j.ijpharm.2020.119276. PMID 32243971. S2CID 214785913.
  5. ^ a b Itin C, Domb AJ, Hoffman A (October 2019). "A meta-opinion: cannabinoids delivered to oral mucosa by a spray for systemic absorption are rather ingested into gastro-intestinal tract: the influences of fed / fasting states". Expert Opinion on Drug Delivery. 16 (10): 1031–1035. doi:10.1080/17425247.2019.1653852. PMID 31393180. S2CID 199505274.
  6. ^ "Sativex (Cannabidiol/Tetrahydrocannabinol) Bayer Label" (PDF). bayer.ca. Archived (PDF) from the original on January 16, 2021. Retrieved June 28, 2018.
  7. ^ a b c "Epidiolex – cannabidiol solution". DailyMed. August 26, 2020. Archived from the original on February 25, 2021. Retrieved September 11, 2020.
  8. ^ https://www.dea.gov/press-releases/2019/08/26/dea-announces-steps-necessary-improve-access-marijuana-research
  9. ^ https://www.law.cornell.edu/uscode/text/7/1639o
  10. ^ Anvisa (July 24, 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published July 25, 2023). Archived from the original on August 27, 2023. Retrieved August 27, 2023.
  11. ^ Cite error: The named reference Home Office was invoked but never defined (see the help page).
  12. ^ "Epidyolex EPAR". European Medicines Agency (EMA). June 24, 2019. Archived from the original on August 9, 2021. Retrieved September 11, 2020. Text was copied from this source which is copyrighted by the European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  13. ^ Perucca E, Bialer M (June 5, 2020). "Critical Aspects Affecting Cannabidiol Oral Bioavailability and Metabolic Elimination, and Related Clinical Implications". CNS Drugs. 34 (8): 795–800. doi:10.1007/s40263-020-00741-5. PMID 32504461. S2CID 219313952.
  14. ^ Scuderi C, Filippis DD, Iuvone T, Blasio A, Steardo A, Esposito G (May 2009). "Cannabidiol in medicine: a review of its therapeutic potential in CNS disorders". Phytotherapy Research (Review). 23 (5): 597–602. doi:10.1002/ptr.2625. PMID 18844286. S2CID 21836765. Archived from the original on April 11, 2021. Retrieved May 22, 2020.
  15. ^ Cite error: The named reference devinsky was invoked but never defined (see the help page).
  16. ^ a b Campos AC, Moreira FA, Gomes FV, Del Bel EA, Guimarães FS (December 2012). "Multiple mechanisms involved in the large-spectrum therapeutic potential of cannabidiol in psychiatric disorders". Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences (Review). 367 (1607): 3364–3378. doi:10.1098/rstb.2011.0389. PMC 3481531. PMID 23108553.
  17. ^ Kirkland AE, Fadus MC, Gruber SA, Gray KM, Wilens TE, Squeglia LM (February 2022). "A scoping review of the use of cannabidiol in psychiatric disorders". Psychiatry Research. 308: 114347. doi:10.1016/j.psychres.2021.114347. PMC 8799523. PMID 34952255.
  18. ^ Black N, Stockings E, Campbell G, Tran LT, Zagic D, Hall WD, et al. (December 2019). "Cannabinoids for the treatment of mental disorders and symptoms of mental disorders: a systematic review and meta-analysis". The Lancet. Psychiatry. 6 (12): 995–1010. doi:10.1016/S2215-0366(19)30401-8. PMC 6949116. PMID 31672337.
  19. ^ a b VanDolah HJ, Bauer BA, Mauck KF (September 2019). "Clinicians' Guide to Cannabidiol and Hemp Oils". Mayo Clinic Proceedings. 94 (9): 1840–1851. doi:10.1016/j.mayocp.2019.01.003. PMID 31447137.
  20. ^ Prud'homme M, Cata R, Jutras-Aswad D (January 2015). "Cannabidiol as an Intervention for Addictive Behaviors: A Systematic Review of the Evidence". Substance Abuse. 9: 33–38. doi:10.4137/SART.S25081. PMC 4444130. PMID 26056464.
  21. ^ Cite error: The named reference sbm was invoked but never defined (see the help page).
  22. ^ a b Pisanti S, Malfitano AM, Ciaglia E, Lamberti A, Ranieri R, Cuomo G, et al. (July 2017). "Cannabidiol: State of the art and new challenges for therapeutic applications". Pharmacology & Therapeutics. 175: 133–150. doi:10.1016/j.pharmthera.2017.02.041. PMID 28232276.
  23. ^ Iseger TA, Bossong MG (March 2015). "A systematic review of the antipsychotic properties of cannabidiol in humans". Schizophrenia Research. 162 (1–3): 153–161. doi:10.1016/j.schres.2015.01.033. PMID 25667194. S2CID 3745655.
  24. ^ Boggs DL, Nguyen JD, Morgenson D, Taffe MA, Ranganathan M (January 2018). "Clinical and Preclinical Evidence for Functional Interactions of Cannabidiol and Δ9-Tetrahydrocannabinol". Neuropsychopharmacology. 43 (1): 142–154. doi:10.1038/npp.2017.209. PMC 5719112. PMID 28875990.
  25. ^ Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, et al. (February 2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products. 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. hdl:1874/350973. PMID 26836472. Archived from the original on January 5, 2023. Retrieved November 27, 2022.
  26. ^ Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, et al. (April 2021). "CBD, a precursor of THC in e-cigarettes". Scientific Reports. 11 (1): 8951. Bibcode:2021NatSR..11.8951C. doi:10.1038/s41598-021-88389-z. PMC 8076212. PMID 33903673.
  27. ^ Mead A (June 14, 2019). "Legal and Regulatory Issues Governing Cannabis and Cannabis-Derived Products in the United States". Frontiers in Plant Science. 10: 697. doi:10.3389/fpls.2019.00697. PMC 6590107. PMID 31263468.
  28. ^ "FDA Regulation of Cannabis and Cannabis-Derived Products, Including Cannabidiol (CBD). #2. How does the 2018 Farm Bill define hemp? What does it mean for FDA-regulated products?". US Food and Drug Administration (FDA). February 6, 2024. Retrieved February 6, 2024.

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