|Systematic (IUPAC) name|
|Bioavailability||13-19% (oral), 11-45% (mean 31%; inhaled)|
|Biological half-life||9 h|
|Melting point||66 °C (151 °F)|
|Boiling point||180 °C (356 °F)
(range: 160–180 °C)
|Part of the Drug series on|
Cannabidiol (CBD) is one of at least 85 active cannabinoids identified in cannabis. It is a major phytocannabinoid, accounting for up to 40% of the plant's extract. CBD is considered to have a wider scope of potential medical applications than tetrahydrocannabinol (THC).
- 1 Research
- 2 CBD-enhanced cannabis
- 3 Industrial hemp
- 4 Pharmacodynamics
- 5 Pharmacokinetic interactions
- 6 Pharmaceutical preparations
- 7 Isomerism
- 8 Chemistry
- 9 Legal status
- 10 References
- 11 External links
Cannabidiol has been listed in EU Cosmetics Ingredient Database with four functional claims: - ANTIOXIDANT - ANTISEBORRHOEIC - SKIN CONDITIONING - SKIN PROTECTING
Cannabidiol has been seen to be an anticonvulsant in animals, but controlled studies in humans are lacking. Randomized trials in treatment-resistant epilepsy syndromes are planned in 2015.
Transdermal CBD is neuroprotective in animals.
Dravet syndrome is a rare form of epilepsy that is difficult to treat. It is a catastrophic form of intractable epilepsy that begins in infancy. Initial seizures are most often prolonged events and in the second year of life other seizure types begin to emerge. A number of high profile and anecdotal reports have sparked interest in treatment of Dravet snydrome with CBD. GW Pharmaceuticals is seeking FDA approval to market a formulation of CBD, under the tradename Epidiolex, as a treatment for Dravet syndrome. Epidiolex was granted fast-track status and is in late stage trials following positive early results from the drug. Some cannabis extract preparations containing CBD are marketed as dietary supplements and claim efficacy against Dravet Syndrome. One such preparation is marketed under the tradename Charlotte's web.
A 2014 Cochrane Review concluded that the evidence is insufficient to conclude that CBD has anti-psychotic effects. Others have concluded it may have antipsychotic effects and may counteract the potential psychotomimetic effects of THC on individuals with latent schizophrenia; some reports show it to be an alternative treatment for schizophrenia that is safe and well-tolerated. Studies have shown CBD may reduce schizophrenic symptoms due to its apparent ability to stabilize disrupted or disabled NMDA receptor pathways in the brain, which are shared and sometimes contested by norepinephrine and GABA. Studies have shown cannabidiol decreases activity of the limbic system  and decreases social isolation induced by THC in rats.
Chronic cannabidiol administration in rats was found to produce reactions suggesting anxiety, indicating that prolonged treatment with cannabidiol might lead to anxiety. Those results have been contested by Gururajan, and contradict Réus, whose experimentation cover the same duration.
Selective breeding by growers in the USA dramatically lowered the CBD content of cannabis; their customers preferred varietals that were more mind-altering due to a higher THC, lower CBD content. To meet the demands of medical cannabis patients, growers are currently developing more CBD-rich strains.
Several industrial hemp varieties can be legally cultivated in western Europe. A variety such as "Fedora 17" has a cannabinoid profile consistently around 1% cannabidiol (CBD) with THC less than 0.1%.
Cannabidiol has a very low affinity for CB1 and CB2 receptors but acts as an indirect antagonist of their agonists. While one would assume that this would cause cannabidiol to reduce the effects of THC, it may potentiate THC's effects by increasing CB1 receptor density or through another CB1-related mechanism. It may also extend the duration of the effects of THC via inhibition of the cytochrome P-450-3A and 2C enzymes.
Recently, it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen. Cannabidiol has also been shown to act as a 5-HT1A receptor partial agonist, an action which may be involved in its antidepressant, anxiolytic, and neuroprotective effects. Cannabidiol is an allosteric modulator of μ and δ-opioid receptors. Cannabidiol's pharmacological effects have also been attributed to PPAR-γ receptor agonism and intracellular calcium release.
Research suggests that CBD may exert some of its pharmacological action through its inhibition of FAAH, which may in turn increase the levels of endocannabinoids, such as anandamide, produced by the body.
There is some preclinical evidence to suggest that cannabidiol may reduce THC clearance, modestly increasing THC's plasma concentrations resulting in a greater amount of THC available to receptors, increasing the effect of THC in a dose-dependent manner. Despite this the available evidence in humans suggests no significant effect of CBD on THC plasma levels.
Nabiximols (USAN, trade name Sativex) is an aerosolized mist for oral administration containing a near 1:1 ratio of CBD and THC. The drug was approved by Canadian authorities in 2005 to alleviate pain associated with multiple sclerosis.
Epidiolex is an oil formulation of CBD extracted from the cannabis plant undergoing clinical trials for refractory epilepsy syndromes.
|7 double bond isomers and their 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 and 3||2-(6-isopropenyl-3-methyl-5-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol||Δ4-cannabidiol||1 and 3||4||No||unscheduled|
|Δ4-cannabidiol||1, 3 and 6||2-(6-isopropenyl-3-methyl-4-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol||Δ5-cannabidiol||1, 3 and 4||8||No||unscheduled|
|Δ3-cannabidiol||1 and 6||2-(6-isopropenyl-3-methyl-3-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol||Δ6-cannabidiol||3 and 4||4||?||unscheduled|
|Δ3,7-cannabidiol||1 and 6||2-(6-isopropenyl-3-methylenecyclohex-1-yl)-5-pentyl-1,3-benzenediol||Δ1,7-cannabidiol||3 and 4||4||No||unscheduled|
|Δ2-cannabidiol||1 and 6||2-(6-isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol||Δ1-cannabidiol||3 and 4||4||Yes||unscheduled|
|Δ1-cannabidiol||3 and 6||2-(6-isopropenyl-3-methyl-1-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol||Δ2-cannabidiol||1 and 4||4||No||unscheduled|
Cannabidiol is insoluble in water but soluble in organic solvents such as pentane. At room temperature, it is a colorless crystalline solid. In strongly basic media and the presence of air, it is oxidized to a quinone. Under acidic conditions it cyclizes to THC. The synthesis of cannabidiol has been accomplished by several research groups.
Cannabidiol is not scheduled by the Convention on Psychotropic Substances.
Legal status in Canada
Cannabidiol is a Schedule II drug in Canada. The newly installed Trudeau government has made full legalization a priority.
Legal status in the United States
||This section possibly contains original research. (November 2015)|
The legal status of Cannabidiol in the United States at the federal level is not immediately clear. The Controlled Substances Act (CSA) does not specifically list cannabidiol in Schedule I nor in any of the other schedules, However, public statements by the Drug Enforcement Administration have long represented cannabidiol as Schedule I.
The drug Schedules list "Tetrahydrocannabinols" and "marijuana" both as Schedule I drugs under the Controlled Substances Act, cannabidiol is not considered as a Schedule I drug on the basis of being covered by the listing of "Marihuana" or by the listing of "Tetrahydrocannabinols" under Schedule I of the CSA. Under current legislation, Cannabidiol as a singular substance does not fall under the criteria set forth under these guidelines, and is currently regarded as GRAS, or "Generally Regarded As Safe" by default.
- "Marijuana" has a DEA Drug Code of 7360 (distinct from cannabidiol's Drug Code of 7372) and is defined by the CSA as "all parts of the plant Cannabis sativa L., whether growing or not; the seeds thereof; the resin extracted from any part of such plant; and every compound, manufacture, salt, derivative, mixture, or preparation of such plant, its seeds or resin." Exempted from regulation under the definition are "the mature stalks of such plant, fiber produced from such stalks, oil or cake made from the seeds of such plant, any other compound, manufacture, salt, derivative, mixture, or preparation of such mature stalks (except the resin extracted therefrom), fiber, oil, or cake, or the sterilized seed of such plant which is incapable of germination." A DEA Interpretive Rule published in 2001 states that the "definition of marijuana was intended to include those parts of marijuana which contain THC and to exclude those parts which do not. ... The legislative history is absolutely clear that Congress meant to outlaw all plants popularly known as marijuana to the extent those plants possessed THC." Cannabidiol isolated by extraction from marijuana sources does not contain THC, and synthetically produced cannabidiol does not contain THC either. It therefore stands to reason that cannabidiol is not covered under the prohibition on marijuana.
- "Tetrahydrocannabinols" listed under Schedule I of the CSA are unlikely to include cannabidiol. Tetrahydrocannabinols are defined as follows:
Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the term "isomer" includes the optical, position and geometric isomers):
- (31) Tetrahydrocannabinols (DEA Drug Code: 7370)
- Meaning tetrahydrocannabinols naturally contained in a plant of the genus Cannabis (cannabis plant), as well as synthetic equivalents of the substances contained in the cannabis plant, or in the resinous extractives of such plant, and/or synthetic substances, derivatives, and their isomers with similar chemical structure and pharmacological activity to those substances contained in the plant, such as the following:
- 1 cis or trans tetrahydrocannabinol, and their optical isomers
- 6 cis or trans tetrahydrocannabinol, and their optical isomers
- 3,4 cis or trans tetrahydrocannabinol, and its optical isomers
- (Since nomenclature of these substances is not internationally standardized, compounds of these structures, regardless of numerical designation of atomic positions covered.)
Since cannabidiol is chemically not a tetrahydrocannabinol (nor indeed a "cannabinol" of any kind) and cannabidiol has a DEA Drug Code of 7372 (distinct from Tetrahydrocannabinols' designated Drug Code of 7370), it stands to reason that cannabidiol is not considered one of the drugs placed into Schedule I under the listing of "Tetrahydrocannabinols" in the CSA.
Furthermore, cannabidiol was not placed into Schedule I when The Controlled Substances Act was amended in July 2012 with the US Congress' passing of the Synthetic Drug Abuse Prevention Act of 2012 (SDAPA) (which came into effect on January 4, 2013) to ban various cannabinoids, cathinones, and phenethylamines. The part adding to Schedule I various "cannabimimetic agents" which include molecules more closely resembling so-called "classically" structured cannabinoids reads as follows:
(1) Unless specifically exempted or unless listed in another schedule, any material, compound, mixture, or preparation which contains any quantity of cannabimimetic agents, or which contains their salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation.
- (2) In paragraph (1):
- (A) The term "cannabimimetic agents" means any substance that is a cannabinoid receptor type 1 (CB1 receptor) agonist as demonstrated by binding studies and functional assays within any of the following structural classes:
- (i) 2-(3-hydroxycyclohexyl)phenol with substitution at the 5-position of the phenolic ring by alkyl or alkenyl, whether or not substituted on the cyclohexyl ring to any extent.
Cannabidiol, while being a more "classically structured" cannabinoid (not like the much more recently discovered cannabinoid receport agonists with indole rings such as many of the JWH- and AM- named series), was not on the list of specifically newly banned cannabinoids (even among those with a more so-called "classic structure"), and it does not fall into the category of unlisted cannabinoids which are caught by the definition above for several reasons. Primarily, CBD is not a CB1 agonist; it is a CB1 antagonist. Also, unlike CP 47,497's homologues and similar synthetic "classical structured cannabinoids" which the above definition was written carefully to include, the cannabidiol molecule has a cyclohexene ring where the amended law requires a cyclohexane ring, and further cannabidiol does not have the required 3-hydroxyl moiety bonded to its cyclohexenyl functional group where the law requires a hydroxyl moiety bonded to the 3- position of a cyclohexyl functional group.
Extracts and concentrates of hemp products which are high in cannabidiol content are very likely legal under US federal law as long as they meet certain requirements. Marihuana is defined by 21 U.S.C. §802(16), which is part of the Controlled Substances Act, and it has a DEA Number / Drug Code of 7360. Exempted from regulation under the definition of marihana is "the mature stalks of such plant, fiber produced from such stalks, oil or cake made from the seeds of such plant, any other compound, manufacture, salt, derivative, mixture, or preparation of such mature stalks (except the resin extracted therefrom), fiber, oil, or cake, or the sterilized seed of any such plant which is incapable of germination." Under this exception, what are known as industrial hemp-finished products are legally imported into the United States each year. Hemp finished products, including hemp oil and extracts of hemp products which are high in cannabidiol, are legal in the United States for this reason.
- Mechoulam R, Parker LA, Gallily R (November 2002). "Cannabidiol: an overview of some pharmacological aspects". J Clin Pharmacol (Review) 42 (11 Suppl): 11S–19S. doi:10.1177/0091270002238789. PMID 12412831.
- 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". Phytother Res (Review) 23 (5): 597–602. doi:10.1002/ptr.2625. PMID 18844286.
- [unreliable medical source?] McPartland JM, Russo EB (2001). "Cannabis and cannabis extracts: greater than the sum of their parts?" (PDF). Journal of Cannabis Therapeutics 1 (3/4): 103–132. doi:10.1300/J175v01n03_08.
- Borgelt LM, Franson KL, Nussbaum AM, Wang GS (February 2013). "The pharmacologic and clinical effects of medical cannabis". Pharmacotherapy (Review) 33 (2): 195–209. doi:10.1002/phar.1187. PMID 23386598.
- 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". Philos. Trans. R. Soc. Lond., B, Biol. Sci. (Review) 367 (1607): 3364–78. doi:10.1098/rstb.2011.0389. PMC 3481531. PMID 23108553.
- Devinsky, Orrin; Cilio, Maria Roberta; Cross, Helen; Fernandez-Ruiz, Javier; French, Jacqueline; Hill, Charlotte; Katz, Russell; Di Marzo, Vincenzo; Jutras-Aswad, Didier (2014-06-01). "Cannabidiol: pharmacology and potential therapeutic role in epilepsy and other neuropsychiatric disorders". Epilepsia 55 (6): 791–802. doi:10.1111/epi.12631. ISSN 1528-1167. PMID 24854329.
- Liput DJ, Hammell DC, Stinchcomb AL, Nixon K (2013). "Transdermal delivery of cannabidiol attenuates binge alcohol-induced neurodegeneration in a rodent model of an alcohol use disorder". Pharmacology Biochemistry and Behavior 111: 120–7. doi:10.1016/j.pbb.2013.08.013. PMID 24012796.
- http://www.dravetfoundation.org/dravet-syndrome/what-is-dravet-syndrome#sthash.jAC0bZ89.dpuf What is Dravet Syndrome?
- Melville, Nancy A. (14 Aug 2013), Seizure Disorders Enter Medical Marijuana Debate, Medscape Medical News., retrieved 2014-01-14
- Throckmorton, Douglas (24 June 2015). "Cannabidiol: Barriers to Research and Potential Medical Benefits". FDA. FDA. Retrieved 15 December 2015.
- Gloss D, Vickrey B (13 June 2012). "Cannabinoids for epilepsy". Cochrane Database Syst Rev (Review) 6: CD009270. doi:10.1002/14651858.CD009270.pub2. PMID 22696383.
- Devinsky, Orrin (2015). "Efficacy and Safety of Epidiolex (Cannabidiol) in Children and Young Adults with Treatment-Resistant Epilepsy". Annual Meeting Abstracts (American Epilepsy Society). Retrieved 13 December 2015.
- Angus, Chen (8 December 2015). "Marijuana's Main Ingredient, Cannabidiol, May Be An Effective Way To Treat Epilepsy". Medical Daily. Retrieved 14 December 2015.
- Maa, Edward; Figi, Paige (2014). "The case for medical marijuana in epilepsy". Epilepsia 55 (6): 783–786. doi:10.1111/epi.12610. ISSN 0013-9580.
- Young, Saundra. "Marijuana stops child's severe seizures" (PDF). CNN. CNN. Retrieved 7 January 2016.
- McLoughlin BC, Pushpa-Rajah JA, Gillies D, Rathbone J, Variend H, Kalakouti E, Kyprianou K (2014). "Cannabis and schizophrenia". Cochrane Database Syst Rev 10: CD004837. doi:10.1002/14651858.CD004837.pub3. PMID 25314586.
- Zuardi AW, Crippa JA, Hallak JE, Moreira FA, Guimarães FS (April 2006). "Cannabidiol, a Cannabis sativa constituent, as an antipsychotic drug". Braz. J. Med. Biol. Res. (Review) 39 (4): 421–9. doi:10.1590/S0100-879X2006000400001. PMID 16612464.
- Long LE, Malone DT, Taylor DA (2005). "Cannabidiol Reverses MK-801-Induced Disruption of Prepulse Inhibition in Mice". Neuropsychopharmacology 31 (4): 795–803. doi:10.1038/sj.npp.1300838. PMID 16052245.
- Crippa JA, Zuardi AW, Garrido GE, Wichert-Ana L, Guarnieri R, Ferrari L, Azevedo-Marques PM, Hallak JE, McGuire PK, Filho Busatto G (October 2003). "Effects of Cannabidiol (CBD) on Regional Cerebral Blood Flow". Neuropsychopharmacology 29 (2): 417–426. doi:10.1038/sj.npp.1300340. PMID 14583744.
- Malone DT, Jongejan D, Taylor DA (August 2009). "Cannabidiol reverses the reduction in social interaction produced by low dose Δ9-tetrahydrocannabinol in rats". Pharmacology Biochemistry and Behavior 93 (2): 91–96. doi:10.1016/j.pbb.2009.04.010. PMID 19393686.
- ElBatsh MM, Assareh N, Marsden CA, Kendall DA (May 2012). "Anxiogenic-like effects of chronic cannabidiol administration in rats". Psychopharmacology 221 (2): 239–247. doi:10.1007/s00213-011-2566-z. PMID 22083592.
- Gururajan A (2012). "Comment on: "Anxiogenic-like effects of chronic cannabidiol administration in rats" (Elbatsh MM, Assareh N, Marsden CA, Kendall DA, Psychopharmacology 2012)". Psychopharmacology 222 (4): 725–6; author reply 727. doi:10.1007/s00213-012-2780-3. PMID 22760485.
- Réus GZ, Stringari RB, Ribeiro KF, Luft T, Abelaira HM, Fries GR, Aguiar BW, Kapczinski F, Hallak JE, Zuardi AW, Crippa JA, Quevedo J (2011). "Administration of cannabidiol and imipramine induces antidepressant-like effects in the forced swimming test and increases brain-derived neurotrophic factor levels in the rat amygdala". Acta Neuropsychiatrica 23 (5): 241–248. doi:10.1111/j.1601-5215.2011.00579.x. PMID 25379896.
- Romney, Lee (13 September 2012). "On the frontier of medical pot to treat boy's epilepsy". Los Angeles Times.
- Good, Alastair (26 October 2010). "Growing marijuana that won't get you high". The Daily Telegraph (London).
- Fournier, G.; Beherec, O.; Bertucelli, S. (2003). "Intérêt du rapport Δ-9-THC / CBD dans le contrôle des cultures de chanvre industriel". Annales de Toxicologie Analytique 15 (4): 250–259. doi:10.1051/ata/2003003.
- Mechoulam R, Peters M, Murillo-Rodriguez E, Hanus LO (August 2007). "Cannabidiol--recent advances". Chem. Biodivers. (Review) 4 (8): 1678–92. doi:10.1002/cbdv.200790147. PMID 17712814.
- Pertwee RG (2008). "The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: Δ9-tetrahydrocannabinol, cannabidiol and Δ9-tetrahydrocannabivarin". British Journal of Pharmacology 153 (2): 199–215. doi:10.1038/sj.bjp.0707442. PMC 2219532. PMID 17828291.
- Hayakawa K, Mishima K, Hazekawa M, Sano K, Irie K, Orito K, Egawa T, Kitamura Y, Uchida N, Nishimura R, Egashira N, Iwasaki K, Fujiwara M (2008). "Cannabidiol potentiates pharmacological effects of Δ9-tetrahydrocannabinol via CB1 receptor-dependent mechanism". Brain Research 1188: 157–164. doi:10.1016/j.brainres.2007.09.090. PMID 18021759.
- Alchimia Blog, Cannabinoids and their medicinal properties
- Ryberg E, Larsson N, Sjögren S, Hjorth S, Hermansson NO, Leonova J, Elebring T, Nilsson K, Drmota T, Greasley PJ (2007). "The orphan receptor GPR55 is a novel cannabinoid receptor". British Journal of Pharmacology 152 (7): 1092–101. doi:10.1038/sj.bjp.0707460. PMC 2095107. PMID 17876302.
- Russo EB, Burnett A, Hall B, Parker KK (August 2005). "Agonistic properties of cannabidiol at 5-HT1a receptors". Neurochemical Research 30 (8): 1037–43. doi:10.1007/s11064-005-6978-1. PMID 16258853.
- Zanelati TV, Biojone C, Moreira FA, Guimarães FS, Joca SR (January 2010). "Antidepressant-like effects of cannabidiol in mice: possible involvement of 5-HT1A receptors". British Journal of Pharmacology 159 (1): 122–8. doi:10.1111/j.1476-5381.2009.00521.x. PMC 2823358. PMID 20002102.
- Resstel LB, Tavares RF, Lisboa SF, Joca SR, Corrêa FM, Guimarães FS (January 2009). "5-HT1A receptors are involved in the cannabidiol-induced attenuation of behavioural and cardiovascular responses to acute restraint stress in rats". British Journal of Pharmacology 156 (1): 181–8. doi:10.1111/j.1476-5381.2008.00046.x. PMC 2697769. PMID 19133999.
- Campos AC, Guimarães FS (August 2008). "Involvement of 5HT1A receptors in the anxiolytic-like effects of cannabidiol injected into the dorsolateral periaqueductal gray of rats". Psychopharmacology 199 (2): 223–30. doi:10.1007/s00213-008-1168-x. PMID 18446323.
- Mishima K, Hayakawa K, Abe K, Ikeda T, Egashira N, Iwasaki K, Fujiwara M (May 2005). "Cannabidiol prevents cerebral infarction via a serotonergic 5-hydroxytryptamine1A receptor-dependent mechanism". Stroke; a Journal of Cerebral Circulation 36 (5): 1077–82. doi:10.1161/01.STR.0000163083.59201.34. PMID 15845890.
- Hayakawa K, Mishima K, Nozako M, Ogata A, Hazekawa M, Liu AX, Fujioka M, Abe K, Hasebe N, Egashira N, Iwasaki K, Fujiwara M (March 2007). "Repeated treatment with cannabidiol but not Delta9-tetrahydrocannabinol has a neuroprotective effect without the development of tolerance". Neuropharmacology 52 (4): 1079–87. doi:10.1016/j.neuropharm.2006.11.005. PMID 17320118.
- Kathmann M, Flau K, Redmer A, Tränkle C, Schlicker E (2006). "Cannabidiol is an allosteric modulator at mu- and delta-opioid receptors". Naunyn-Schmiedeberg's Archives of Pharmacology 372 (5): 354–361. doi:10.1007/s00210-006-0033-x. PMID 16489449.
- Campos, A. C.; Moreira, F. A.; Gomes, F. V.; Del Bel, E. A.; Guimaraes, F. S. (2012). "Multiple mechanisms involved in the large-spectrum therapeutic potential of cannabidiol in psychiatric disorders". Philosophical Transactions of the Royal Society B: Biological Sciences 367 (1607): 3364–3378. doi:10.1098/rstb.2011.0389. ISSN 0962-8436. PMC 3481531. PMID 23108553.
- Bornheim LM, Kim KY, Li J, Perotti BY, Benet LZ (August 1995). "Effect of cannabidiol pretreatment on the kinetics of tetrahydrocannabinol metabolites in mouse brain". Drug Metabolism and Disposition 23 (8): 825–831. PMID 7493549.
- Klein C, Karanges E, Spiro A, Wong A, Spencer J, Huynh T, Gunasekaran N, Karl T, Long LE, Huang XF, Liu K, Arnold JC, McGregor IS (November 2011). "Cannabidiol potentiates Δ⁹-tetrahydrocannabinol (THC) behavioural effects and alters THC pharmacokinetics during acute and chronic treatment in adolescent rats". Psychopharmacology 218 (2): 443–457. doi:10.1007/s00213-011-2342-0. PMID 21667074.
- Hunt CA, Jones RT, Herning RI, Bachman J (June 1981). "Evidence that Cannabidiol Does Not Significantly Alter the Pharmacokinetics of Tetrahydrocannabinol in Man". Journal of Pharmacokinetics and Biopharmaceutics 9 (3): 245–260. doi:10.1007/BF01059266. PMID 6270295.
- United States Adopted Names Council: Statement on a nonproprietary name
- "Fact Sheet — Sativex". Health Canada. Retrieved 16 May 2013.
- GWPharma- Welcome
- "Georgia doctors encouraged in study of medical marijuana". Retrieved 2015-10-08.
- Jones PG, Falvello L, Kennard O, Sheldrick GM Mechoulam R (1977). "Cannabidiol". Acta Cryst. B33 (10): 3211–3214. doi:10.1107/S0567740877010577.
- Mechoulam R, Ben-Zvi Z, Gaoni Y (1968). "Hashish—XIII On the nature of the beam test". Tetrahedron 24 (16): 5615–5624. doi:10.1016/0040-4020(68)88159-1. PMID 5732891.
- 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.
- Petrzilka T, Haefliger W, Sikemeier C, Ohloff G, Eschenmoser A (1967). "Synthese und Chiralität des (−)-Cannabidiols". Helv. Chim. Acta 50 (2): 719–723. doi:10.1002/hlca.19670500235. PMID 5587099.
- 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.
- Kobayashi Y, Takeuchi A, Wang YG (2006). "Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate". Org. Lett. 8 (13): 2699–2702. doi:10.1021/ol060692h. PMID 16774235.
- 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 Δ9-tetrahydrocannabinol biosynthesis in Cannabis sativa". Journal of Experimental Botany 60 (13): 3715–3726. doi:10.1093/jxb/erp210. PMC 2736886. PMID 19581347.
- Controlled Drugs and Substances Act – Schedule II
- §1308.11 Schedule I.
- Controlled Substances by CSA Schedule – September 2014
- Title 21 US Code Controlled Substances Act, §802. Definitions.
- , SCHEDULE AND DRUG CODES
- Rules – 2013 > Establishment of Drug Codes for 26 Substances
- Synthetic Drug Abuse Prevention Act of 2012 – GovTrack.us
- Russo EB (August 2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects". Br. J. Pharmacol. (Review) 163 (7): 1344–64. doi:10.1111/j.1476-5381.2011.01238.x. PMC 3165946. PMID 21749363.
- Morgan, C. J. (October 2010). "Impact of cannabidiol on the acute memory and psychotomimetic effects of smoked cannabis: naturalistic study: naturalistic study [corrected].". British Journal of Psychiatry 197 (4): 285–90. doi:10.1192/bjp.bp.110.077503. PMID 20884951.
- Definition of marijuana under the Controlled Substances Act.
- Hemp Industries Assn., v. Drug Enforcement Admin., 9th Circuit Court of Appeals case involving industrial hemp.
- Hemp, Many definitions of common terms associated with hemp, including the history of hemp use.
- Project CBD Non-profit educational service dedicated to promoting and publicizing research into the medical utility of cannabidiol.