Cannabidiol

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Cannabidiol
230px
230px
Systematic (IUPAC) name
2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Legal status
Legal status
  • Schedule II (Can)
    Unscheduled (USA)
Identifiers
CAS Number 13956-29-1
ATC code noentry (WHO)
PubChem CID 644019
DrugBank none
ChemSpider 559095
Chemical data
Formula C21H30O2
Molar mass 314.46[[Script error: No such module "String".]]
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Physical data
Melting point 66 °C (151 °F)
Boiling point 180 °C (356 °F)
(Range: 160°C-180°C) [1]
  (verify)
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Cannabidiol (CBD) is a cannabinoid found in Cannabis. It is a major constituent of the plant, representing up to 40% in its extracts.[2]

It has displayed sedative effects in animal tests.[3] Some research, however, indicates that CBD can increase alertness.[4] It may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver.

Medically, it has been shown to relieve convulsion, inflammation, anxiety, and nausea, as well as inhibit cancer cell growth[5] Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia.[6] Studies have also shown that it may relieve symptoms of dystonia.[7][8]

In November 2007, it was reported that CBD reduces growth of aggressive human breast cancer cells in vitro and reduces their invasiveness.

A 2008 study published in the British Journal of Psychiatry showed significant differences in Oxford-Liverpool Inventory of Feelings and Experiences scores between three groups: The first consisted of non-cannabis users, the second of users who tested positive for Δ9-THC only, and the third consisted of users who tested positive for both Δ9-THC and CBD. The Δ9-THC only subset scored significantly higher for unusual experiences, while users of both Δ9-THC and CBD had much lower introvertive anhedonia scores.[9]

Medicinal use

Cannabidiol is shown to decrease activity of limbic system[10] and to decrease social isolation induced by THC.[11]

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.

Studies have shown that CBD may reduce schizophrenic symptoms in patients.[6] Leweke et al. performed a double blind, 4 week, explorative controlled clinical trial to compare the effects of purified cannabidiol and the atypical antipsychotic amisulpride on improving the symptoms of schizophrenia in 42 patients with acute paranoid schizophrenia. Both treatments were associated with a significant decrease of psychotic symptoms after 2 and 4 weeks as assessed by Brief Psychiatric Rating Scale and Positive and Negative Syndrome Scale. While there was no statistical difference between the two treatment groups, cannabidiol induced significantly less side effects (extrapyramidal symptoms, increase in prolactin, weight gain) when compared to amisulpride.[12]

Cannabidiol has also been shown as being effective treating an often drug-induced set of neurological movement disorders known as dystonia.[8] In one study, five out of five participants showed noted improvement in their dystonic symptoms by 20-50%.[7]

Pharmacology

Cannabidiol has no affinity for CB1 and CB2 receptors but acts as an indirect antagonist of cannabinoid agonists.[5] Recently it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen.[13] Cannabidiol has also been shown to act as a 5-HT1A receptor agonist,[14] an action which is involved in its antidepressant,[15][16] anxiolytic,[17][16] and neuroprotective[18][19] effects.

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."[20] 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 ID1 which is responsible for tumor metastasis.[21]

Chemistry

Cannabidiol is insoluble in water but soluble in organic solvents. At room temperature it is a colorless crystalline solid.[22] In strongly basic medium and the presence of air it is oxidized to a quinone.[23] Under acidic conditions it cyclizes to THC.[24] The synthesis of cannabidiol has been accomplished by several research groups.[25][26][27]

Biosynthesis

Cannabis, produces CBD-carboxylic acid through the same metabolic pathway as THC, until the last step, where CBDA synthase performs catalysis instead of THCA synthase.[28]

Legal Status

In Canada Cannabidiol is a Schedule 2 Drug, a category that encompasses quantities of cannabis less than 30 grams, and various related synthetic derivatives and preparations[29]. In the United States it is unscheduled. Only cannabis (the plant itself) and the tetrahydrocannabinol cannabinoids are listed in DEA Drug Scheduling. [30]

See also

References

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External links

  • Erowid Compounds found in Cannabis sativa


GABAA PAMs
Others
α2δ VDCC Blockers
5-HT1A Agonists
Azapirones: Buspirone • Gepirone • Tandospirone; Others: Flesinoxan • Oxaflozane
H1 Antagonists
Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine • Pheniramine
CRH1 Antagonists
NK2 Antagonists
MCH1 antagonists
mGluR2/3 Agonists
mGluR5 NAMs
TSPO agonists
σ1 agonists
Others

M: PSO/PSI

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc, drug(N5A/5B/5C/6A/6B/6D)

Antipsychotics (neuroleptics) (N05A)
Typical
Benzamides: Levosulpiride • Nemonapride • Sulpiride • Sultopride • Tiapride • Veralipride; Butyrophenones: Azaperone • Benperidol • Bromperidol • Droperidol • Fluanisone • Haloperidol • Lenperone • Moperone • Pipamperone • Spiperone • Timiperone • Trifluperidol; Diphenylbutylpiperidines: Clopimozide • Fluspirilene • Penfluridol • Pimozide; Phenothiazines: Acepromazine • Acetophenazine • Butaperazine • Carphenazine • Chloracizine • Chlorproethazine • Chlorpromazine • Cyamemazine • Dixyrazine • Fluacizine • Fluphenazine • Levomepromazine/Methotrimeprazine • Mesoridazine • Perazine • Periciazine • Perphenazine • Piperacetazine • Pipotiazine • Prochlorperazine • Promazine • Promethazine • Propiomazine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioproperazine • Thioridazine • Trifluoperazine • Triflupromazine; Thioxanthenes: Chlorprothixene • Clopenthixol • Flupentixol • Thiothixene • Zuclopenthixol; Tricyclics: Amoxapine • Butaclamol • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin • Trimipramine; Others: Prothipendyl
Atypical
Others

M: PSO/PSI

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc, drug(N5A/5B/5C/6A/6B/6D)

ca:Cannabidiol

de:Cannabidiol es:Cannabidiol it:Cannabidiolo la:Cannabidiol hu:Kannabidiol pl:Kannabidiol pt:Canabidiol ru:Каннабидиол fi:Kannabidioli

sv:Cannabidiol
  1. ↑ McPartland JM, Russo EB. (2001). Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts?. Journal of Cannabis Therapeutics. 1(3/4):103-132.
  2. ↑ Grlie, L (1976). "A comparative study on some chemical and biological characteristics of various samples of cannabis resin". Bulletin on Narcotics. 14: 37–46. 
  3. ↑ Pickens JT (1981). "Sedative activity of cannabis in relation to its delta'-trans-tetrahydrocannabinol and cannabidiol content". Br. J. Pharmacol. 72 (4): 649–56. PMC 2071638 Freely accessible. PMID 6269680. 
  4. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  7. ↑ 7.0 7.1 Consroe, P; Sandyk, R; Snider, SR (1986). "Open label evaluation of cannabidiol in dystonic movement disorders". The International journal of neuroscience. 30 (4): 277–82. doi:10.3109/00207458608985678. PMID 3793381.  edit
  8. ↑ 8.0 8.1 Snider, Stuart R. and Consroe, Paul. (1985). "Beneficial and Adverse Effects of Cannabidiol in a Parkinson Patient with Sinemet-Induced Dystonic Dyskinesia". Neurology. (Suppl 1) p. 201.
  9. ↑ Celia J. A. Morgan, PhD and H. Valerie Curran, PhD, DClinPsy Effects of cannabidiol on schizophrenia-like symptoms in people who use cannabis
  10. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  11. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  12. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  13. ↑ Ryberg E, Larsson N, Sjögren S; et al. (2007). "The orphan receptor GPR55 is a novel cannabinoid receptor". British Journal of Pharmacology. 152 (7): 1092. doi:10.1038/sj.bjp.0707460. PMC 2095107 Freely accessible. PMID 17876302. 
  14. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  15. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  16. ↑ 16.0 16.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  17. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  18. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  19. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  20. ↑ Ligresti A, Moriello AS, Starowicz K; et al. (2006). "Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma". J. Pharmacol. Exp. Ther. 318 (3): 1375–87. doi:10.1124/jpet.106.105247. PMID 16728591. 
  21. ↑ McAllister SD, Christian RT, Horowitz MP, Garcia A, Desprez PY (2007). "Cannabidiol as a novel inhibitor of Id-1 gene expression in aggressive breast cancer cells". Mol. Cancer Ther. 6 (11): 2921–7. doi:10.1158/1535-7163.MCT-07-0371. PMID 18025276. 
  22. ↑ Jones PG, Falvello L, Kennard O, Sheldrick GM Mechoulam R (1977). "Cannabidiol". Acta Cryst. B33: 3211–3214. doi:10.1107/S0567740877010577. 
  23. ↑ Mechoulam R, Ben-Zvi Z (1968). "Hashish—XIII On the nature of the beam test". Tetrahedron. 24 (16): 5615–5624. doi:10.1016/0040-4020(68)88159-1. 
  24. ↑ 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. 
  25. ↑ 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. 
  26. ↑ 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. 
  27. ↑ 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. 
  28. ↑ Marks, M.; Tian, L.; Wenger, J.; Omburo, S.; Soto-Fuentes, W.; He, J.; Gang, D.; Weiblen, G.; Dixon, R. (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 Freely accessible. PMID 19581347.  edit
  29. ↑ http://laws.justice.gc.ca/en/showdoc/cs/C-38.8//20090606/en?command=search&caller=SI&fragment=schedule%201&search_type=all&day=6&month=6&year=2009&search_domain=cs&showall=L&statuteyear=all&lengthannual=50&length=50&offset=2
  30. ↑ http://www.justice.gov/dea/pubs/scheduling.html
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