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Cannabidiol

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Cannabidiol
type of chemical entity, cannabinoids
Subclass of2-[(6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Edit
Stereoisomer of1,3-Benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, (1R-trans)- Edit
Chemical formulaC₂₁H₃₀O₂ Edit
Canonical SMILESCCCCCC1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O Edit
Isomeric SMILESCCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O Edit
Found insyd taxonCannabis sativa Edit
Physically dey interact plusG protein-coupled receptor 18, G protein-coupled receptor 55, Transient receptor potential cation channel subfamily M member 8, Transient receptor potential cation channel subfamily V member 2 Edit
LiverTox likelihood scoreLiverTox toxicity likelihood category E* Edit

Cannabidiol (CBD) be a phytocannabinoid, one of 113 cannabinoids dem identify insyd Cannabis, along plus tetrahydrocannabinol (THC), wey e dey account for up to 40% of de plant ein extract.[1] Medically, e be an anticonvulsant dem use take treat multiple forms of epilepsy.[2] Na dem discover am insyd 1940 den, as of 2024 clinical research for CBD included studies wey relate to de treatment of anxiety, addiction, psychosis, movement disorders, den pain, buh der be insufficient high-quality evidence dat CBD be effective for dese conditions.[3][4][5][6] Dem dey sell CBD as an herbal dietary supplement wey dem promote am plus yet unproven claims of particular therapeutic effects.[7]

Dem fi take cannabidiol internally insyd chaw ways, wey dey include by inhaling cannabis smoke anaa vapor, dey swallow am by mouth, den thru use of an aerosol spray into de cheek.[8][9] E fi be supplied as CBD oil wey dey contain CBD per as de active ingredient (wey dey exclude THC anaa terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, anaa prescription liquid solution.[2][5] CBD no get de same psychoactivity as Tetrahydrocannabinol (THC),[10][11] wey e fi modulate de psychoactive effects of THC for de body top if both be present.[12][10][13][14] Conversion of CBD to THC fi occur wen CBD be heated to temperatures between 250–300 °C, potentially wey dey lead to ein partial transformation into THC.[15]

Chemistry

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At room temperature, cannabidiol be a colorless crystalline solid.[16] Insyd strongly basic media den de presence of air, e be oxidized to cannabinodiol (CBND) den a quinone wey be called HU-331.[17] Under acidic conditions e dey cyclize to THC,[18] wich sanso dey occur during pyrolysis,[19] den during smoking.[20] Na de synthesis of cannabidiol be accomplished by chaw research groups.[21][22][23]

Possible mechanism of intramolecular cyclization of CBD to Δ9-THC[24]

Overview

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Category Compound Description
Analog 4'-Fluorocannabidiol fluorinated cannabidiol derivative of CBD
Analog Cannabidibutol (CBDB) an analogue to tetrahydrocannabutol (THCB)
Analog Cannabidiol diacetate a semi-synthetic derivative of CBD
Analog Cannabidiol dimethyl ether (CBDD) an analog of CBD
Analog H4-CBD a structural analog of CBD
Analog HU-320 a structural analog of CBD
Analog KLS-13019 a structural analog of CBD
Homologue 8,9-Dihydrocannabidiol (H2CBD) synthetic derivative of CBD
Homologue Cannabidiorcol (CBD-C1) a homologue of CBD
Homologue Cannabidiphorol (CBDP) de heptyl-homologue of CBD
Homologue Cannabidivarin (CBDV) a homologue of CBD
Homologue CBD-DMH synthetic homologue of CBD
Homologue Δ-6-Cannabidiol a positional isomer of CBD
Isomer Abnormal cannabidiol a synthetic regioisomer of CBD
Metabolite 7-Hydroxycannabidiol (7-OH-CBD) an active metabolite of CBD
Precursor Cannabidiolic acid (CBDA) precursor to CBD

Biosynthesis

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Cannabidiol den THC biosynthesis[25]

Cannabis dey produce CBD thru de same metabolic pathway as THC, til de next to last step, wer CBDA synthase dey perform catalysis instead of THCA synthase.[26]

Isomerism

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Cannabidiol numbering
Cannabidiol numbering
Cannabidiol's 7 double bond isomers den dema 30 stereoisomers
Formal numbering Terpenoid numbering Number of stereoisomers Natural occurrence Convention on Psychotropic Substances Schedule Structure
Short name Chiral centers Full name Short name Chiral centers
Δ5-Cannabidiol 1 den 3 2-(6-isopropenyl-3-methyl-5-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ4-Cannabidiol 1 den 3 4 No Unscheduled
Δ4-Cannabidiol 1, 3 den 6 2-(6-isopropenyl-3-methyl-4-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ5-Cannabidiol 1, 3 den 4 8 No Unscheduled
Δ3-Cannabidiol 1 den 6 2-(6-isopropenyl-3-methyl-3-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ6-Cannabidiol 3 den 4 4 Yes Unscheduled
Δ3,7-Cannabidiol 1 den 6 2-(6-isopropenyl-3-methylenecyclohex-1-yl)-5-pentyl-1,3-benzenediol Δ1,7-Cannabidiol 3 den 4 4 No Unscheduled
Δ2-Cannabidiol 1 den 6 2-(6-isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ1-Cannabidiol 3 den 4 4 Yes Unscheduled
Δ1-Cannabidiol 3 den 6 2-(6-isopropenyl-3-methyl-1-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ2-Cannabidiol 1 den 4 4 No Unscheduled
Δ6-Cannabidiol 3 2-(6-isopropenyl-3-methyl-6-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ3-Cannabidiol 1 2 No Unscheduled

Pyrolysis

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Insyd de typical operating temperature range of e-cigarettes (250–400 °C (482–752 °F)), 25–52% of CBD be transformed into oda chemical substances: Δ9-THC, Δ8-THC, cannabinol den cannabichromene as predominant pyrolysates. From a chemical point of view, CBD insyd e-cigarettes fi be considered a precursor of THC.[15]

Synthetic derivatives

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Numerous synthetic derivatives of CBD be known, wey na dem be researched for generally similar applications as CBD einself.[27]

References

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  1. ↑ 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.
  2. ↑ 2.0 2.1 "Epidiolex – cannabidiol solution". DailyMed. August 26, 2020. Archived from the original on February 25, 2021. Retrieved September 11, 2020.
  3. ↑ 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.
  4. ↑ Black N, Stockings E, Campbell G, Tran LT, Zagic D, Hall WD, Farrell M, Degenhardt L (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.
  5. ↑ 5.0 5.1 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.
  6. ↑ 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.
  7. ↑ Novella S (September 30, 2020). "Where Are We With CBD?". Science-Based Medicine. Archived from the original on August 12, 2021. Retrieved October 1, 2020.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 10.0 10.1 Pisanti S, Malfitano AM, Ciaglia E, Lamberti A, Ranieri R, Cuomo G, Abate M, Faggiana G, Proto MC, Fiore D, Laezza C, Bifulco M (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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A (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. Bibcode:2016JNAtP..79..324A. doi:10.1021/acs.jnatprod.5b00949. hdl:1874/350973. PMID 26836472. Archived from the original on January 5, 2023. Retrieved November 27, 2022.
  15. ↑ 15.0 15.1 Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, Csupor-Löffler B, Tóth B, Csupor D (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.
  16. ↑ Jones PG, Falvello L, Kennard O, Sheldrick GM, Mechoulam R (1977). "Cannabidiol". Acta Crystallogr. B. 33 (10): 3211–3214. Bibcode:1977AcCrB..33.3211J. doi:10.1107/S0567740877010577.
  17. ↑ Mechoulam R, Ben-Zvi Z, Gaoni Y (August 1968). "Hashish – 13. On the nature of the Beam test". Tetrahedron. 24 (16): 5615–5624. doi:10.1016/0040-4020(68)88159-1. PMID 5732891.
  18. ↑ Gaoni Y, Mechoulam R (1966). "Hashish – VII The isomerization of cannabidiol to tetrahydrocannabinols". Tetrahedron. 22 (4): 1481–1488. doi:10.1016/S0040-4020(01)99446-3.
  19. ↑ Küppers FJ, Bercht CA, Salemink CA, Lousberg RC, Terlouw JK, Heerma W (1975). "Cannabis – XV: Pyrolysis of cannabidiol. Structure elucidation of four pyrolytic products". Tetrahedron. 31 (13–14): 1513–1516. doi:10.1016/0040-4020(75)87002-5.
  20. ↑ Quarles W, Ellman G, Jones R (1973). "Toxicology of marijuana: conditions for conversion of cannabidiol to THC upon smoking". Clinical Toxicology. 6 (2): 211–216. doi:10.3109/15563657308990520. PMID 4715204.
  21. ↑ Petrzilka T, Haefliger W, Sikemeier C, Ohloff G, Eschenmoser A (March 1967). "[Synthesis and optical rotation of the (-)-cannabidiols]". Helvetica Chimica Acta. 50 (2): 719–723. doi:10.1002/hlca.19670500235. PMID 5587099.
  22. ↑ Gaoni Y, Mechoulam R (1985). "Boron trifluoride etherate on alumuna – a modified Lewis acid reagent. An improved synthesis of cannabidiol". Tetrahedron Letters. 26 (8): 1083–1086. doi:10.1016/S0040-4039(00)98518-6.
  23. ↑ Kobayashi Y, Takeuchi A, Wang YG (June 2006). "Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate". Organic Letters. 8 (13): 2699–2702. doi:10.1021/ol060692h. PMID 16774235.
  24. ↑ Gaoni Y, Mechoulam R (January 1966). "Hashish – VII: The isomerization of cannabidiol to tetrahydrocannabinols". Tetrahedron. 22 (4): 1481–1488. doi:10.1016/S0040-4020(01)99446-3.
  25. ↑ Taura F, Sirikantaramas S, Shoyama Y, Yoshikai K, Shoyama Y, Morimoto S (June 2007). "Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa". FEBS Letters. 581 (16): 2929–2934. Bibcode:2007FEBSL.581.2929T. doi:10.1016/j.febslet.2007.05.043. PMID 17544411. S2CID 20253070.
  26. ↑ Marks MD, Tian L, Wenger JP, Omburo SN, Soto-Fuentes W, He J, Gang DR, Weiblen GD, Dixon RA (2009). "Identification of candidate genes affecting Delta9-tetrahydrocannabinol biosynthesis in Cannabis sativa". Journal of Experimental Botany. 60 (13): 3715–3726. doi:10.1093/jxb/erp210. PMC 2736886. PMID 19581347.
  27. ↑ Nelson KM, Bisson J, Singh G, Graham JG, Chen SN, Friesen JB, Dahlin JL, Niemitz M, Walters MA, Pauli GF (November 2020). "The Essential Medicinal Chemistry of Cannabidiol (CBD)". Journal of Medicinal Chemistry. 63 (21): 12137–12155. doi:10.1021/acs.jmedchem.0c00724. PMC 7666069. PMID 32804502.
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