Cannabidiol

drugbox
IUPAC_name = "2-((1"S",6"S")-3-methyl-6-(prop-1-en-2-yl)
cyclohex-2-enyl)-5-pentylbenzene-1,3-diol"

---

width = 240

---

width2 = 240
CAS_number = 13956-29-1
ATC_prefix = no
ATC_suffix = entry
PubChem = 644019
DrugBank = none
C=21|H=30|O=2
molecular_weight = 314.46
melting_point = 66
smiles = CCCCCC(C=C1O)=CC(O)=C1 [C@] 2
(C=C(C)CC [C@] 2( [H] )C(C)=C) [H]
bioavailability =
metabolism =
elimination_half-life =
excretion =
pregnancy_category =
legal_status = Schedule I (US)
routes_of_administration =

Cannabidiol, also known as CBD, is a cannabinoid found in "Cannabis". It is a major constituent of the plant, representing up to 40% in its extracts.cite journal
last =Grlie
first = L
authorlink =
coauthors =
title =A comparative study on some chemical and biological characteristics of various samples of cannabis resin
journal =Bulletin on Narcotics
volume =14
issue =
pages =37–46
publisher =
date = 1976
url =
doi =
id =
accessdate = ]

CBD alone is not intoxicating, but it appears to moderate the euphoric effect of tetrahydrocannabinol (THC), which is an isomer of cannabidiol and add a sedative quality.cite journal
author=Pickens JT
title=Sedative activity of cannabis in relation to its delta'-trans-tetrahydrocannabinol and cannabidiol content
journal=Br. J. Pharmacol.
volume=72
issue=4
pages=649–56
year=1981
pmid=6269680
doi=] Some research, however, indicates that CBD can increase alertness. [cite journal
last = Nicholson
first = AN
authorlink =
coauthors = C Turner, BM Stone, and PJ Robson
year = 2004
month = June
title = Effect of Delta-9-tetrahydrocannabinol and cannabidiol on nocturnal sleep and early-morning behavior in young adults
journal = J Clin Psychopharmacol
volume = 24
issue = 3
pages = 305–13
issn = 0271-0749
pmid = 15118485
url = http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0271-0749&volume=24&issue=3&spage=305
format = fee required
accessdate = 2007-05-03
doi = 10.1097/01.jcp.0000125688.05091.8f ] It may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver. CBD does not appear to affect either the CB₁ or CB₂ receptors. [cite journal
last = Straus
first = Stephen E.
authorlink =
coauthors =
title = Immunoactive cannabinoids: Therapeutic prospects for marijuana constituents
journal = Proc Natl Acad Sci U S A.
volume = 97
issue = 17
pages = 9363–9364
publisher =
date = 15 August 2000
url = http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=34030#B18
doi =10.1073/pnas.180314297
id =
accessdate =
pmid = 10931962 ]

Medically, it appears to relieve convulsion, inflammation, anxiety, and nausea, and to inhibit cancer cell growth. [cite journal
author=Mechoulam R, Peters M, Murillo-Rodriguez E, Hanus LO
title=Cannabidiol - recent advances
journal=Chemistry & Biodiversity
volume=4
issue=8
pages=1678–1692
year=2007
month=Aug.
pmid=17712814
doi=10.1002/cbdv.200790147] Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia. [cite journal
last = Zuardi
first = A.W
coauthors = J.A.S. Crippa, J.E.C. Hallak, F.A. Moreira, F.S. Guimarães
title = Cannabidiol as an antipsychotic drug
journal = Brazilian Journal of Medical and Biological Research
date = 2006
volume = 39
pages = 421–429
url = http://www.scielo.br/pdf/bjmbr/v39n4/6164.pdf
issn = ISSN 0100-879X ] In November 2007 it was reported that CBD reduces growth of aggressive human breast cancer cells "in vitro" and reduces their invasiveness. It thus represents the first non-toxic exogenous agent that can lead to down-regulation of tumor aggressiveness. [ [http://news.bbc.co.uk/1/hi/health/7098340.stm Article] on BBC site] It is also a neuroprotective antioxidant. [http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=20965 Cannabidiol and (−)Δ9-tetrahydrocannabinol are neuroprotective antioxidants] , A. J. Hampson, M. Grimaldi, J. Axelrod, and D. Wink, Proc Natl Acad Sci U S A. 1998 July 7; 95(14): 8268–8273.]

Medicinal use

In April 2005, Canadian authorities approved the marketing of Sativex, a mouth spray for multiple sclerosis to alleviate pain. Sativex contains tetrahydrocannabinol together with cannabidiol. It is marketed in Canada by GW Pharmaceuticals.

Initial research is showing that CBD has an effect in reducing schizophrenic symptoms in patients, but much more research is needed before any link is confirmed, let alone it being developed into an anti-psychotic medication. [cite journal
last = Zuardi
first = A.W
coauthors = J.A.S. Crippa, J.E.C. Hallak, F.A. Moreira, F.S. Guimarães
title = Cannabidiol as an antipsychotic drug
journal = Brazilian Journal of Medical and Biological Research
date=2006
volume = 39
pages = 421–429
url = http://www.scielo.br/pdf/bjmbr/v39n4/6164.pdf
issn = ISSN 0100-879X ]

Pharmacology

Cannabidiol does not bind to CB₁ or CB₂ receptors but it does block the effects of cannabinoid agonists by an unknown indirect way. [cite journal
author=Thomas A, Baillie GL, Phillips AM, Razdan RK, Ross RA, Pertwee RG
title=Cannabidiol displays unexpectedly high potency as an antagonist of CB₁ and CB₂ receptor agonists in vitro
journal=Br. J. Pharmacol.
volume=150
issue=5 |pages=613–23
year=2007
pmid=17245363
doi=10.1038/sj.bjp.0707133] Recently it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen. [cite journal
author=Ryberg E, Larsson N, Sjögren S, "et al"
title=The orphan receptor GPR55 is a novel cannabinoid receptor
journal= British Journal of Pharmacology
volume= 152
issue=
pages= 1092
year=2007
pmid=17876302
doi=10.1038/sj.bjp.0707460]

Cannabidiol has also been shown to inhibit cancer cell growth, with low potency in non-cancer cells. Although the inhibitory mechanism is not yet fully understood, Ligresti et al suggest that "cannabidiol exerts its effects on these cells through a combination of mechanisms that include either direct or indirect activation of CB₂ and TRPV1 receptors, and induction of oxidative stress, all contributing to induce apoptosis."cite journal
author=Ligresti A, Moriello AS, Starowicz K, "et al"
title=Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma
journal=J. Pharmacol. Exp. Ther.
volume=318
issue=3
pages=1375–87
year=2006
pmid=16728591
doi=10.1124/jpet.106.105247] In November 2007, researchers at the California Pacific Medical Center reported that CBD shows promise for controlling the spread of metastatic breast cancer. "In vitro" CBD downregulates the activity of the gene Id-1 which is responsible for tumor metastasis.cite journal
author=McAllister SD, Christian RT, Horowitz MP, Garcia A, Desprez PY
title=Cannabidiol as a novel inhibitor of Id-1 gene expression in aggressive breast cancer cells
journal=Mol. Cancer Ther.
volume=6
issue=11
pages=2921–7
year=2007
pmid=18025276
doi=10.1158/1535-7163.MCT-07-0371]

Chemistry

Cannabidiol is insoluble in water but soluble in organic solvents. At room temperature it is a colorless crystalline solid. [cite journal
author=Jones PG, Falvello L, Kennard O, Sheldrick GM Mechoulam R
title=Cannabidiol
journal= Acta Cryst.
volume= B33
pages= 3211–3214
year=1977
doi=10.1107/S0567740877010577] In strongly basic medium and the presence of air it is oxidized to a quinone. [cite journal
author=Mechoulam R, Ben-Zvi Z
title=Hashish—XIII On the nature of the beam test
journal= Tetrahedron
volume= 24
issue=16
pages= 5615–5624
year=1968
doi=10.1016/0040-4020(68)88159-1] Under acidic conditions it cyclizes to THC. [cite journal
author=Gaoni Y, Mechoulam R
title=Hashish—VII The isomerization of cannabidiol to tetrahydrocannabinols
journal= Tetrahedron
volume= 22
issue=4
pages= 1481–1488
year=1966
doi=10.1016/S0040-4020(01)99446-3] The synthesis of cannabidiol has been accomplished by several research groups. [cite journal
author=Petrzilka T, Haefliger W, Sikemeier C, Ohloff G, Eschenmoser A
title=Synthese und Chiralität des (-)-Cannabidiols
journal= Helv. Chim. Acta
volume= 50
issue=2
pages= 719–723
year=1967
doi=10.1002/hlca.19670500235] [cite journal
author=Gaoni Y, Mechoulam R
title=Boron trifluoride etherate on alumuna - a modified Lewis acid reagent. An improved synthesis of cannabidiol
journal= Tetrahedron Letters
volume= 26
issue=8
pages= 1083–1086
year=1985
doi=10.1016/S0040-4039(00)98518-6] [cite journal
author=Kobayashi Y, Takeuchi A, Wang YG
title=Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate
journal=Org. Lett.
volume=8
issue=13
pages=2699–2702 |year=2006 |pmid=16774235
doi=10.1021/ol060692h]

Legal Status

Cannabidiol is a Schedule I drug in the USA, despite having no psychoactive effects and no known abuse potential.

References

See also

* Cannabinoids
* Cannabinoid receptors
* Cannabis
* Health issues and the effects of cannabis
* Medical marijuana

External links

* [http://www.erowid.org/plants/cannabis/cannabis_info2.shtml Erowid] Compounds found in "Cannabis sativa"