cannabidiol

Cannabidiol

Systematic (IUPAC) name
2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Identifiers
CAS number	13956-29-1
ATC code	noentry
PubChem	644019
DrugBank	none
ChemSpider	559095
Chemical data
Formula	C21H30O2
Mol. mass	314.46
SMILES	eMolecules & PubChem
Physical data
Melt. point	66 °C (151 °F)
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule II (Can)
Routes	?
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Cannabidiol (CBD) is a psychoactive cannabinoid found in Cannabis. It is a major constituent of the plant, representing up to 40% in its extracts.^[1]

CBD alone is not intoxicating, but displayed sedative effects in animal tests.^[2] Some research, however, indicates that CBD can increase alertness.^[3] It may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver. CBD appears to affect both the CB₁ and CB₂ receptors- with higher affinity for the CB₂ receptors .^[4] Cannabis indica dominant strains of the plant are known to be higher in CBD than Cannabis sativa strains.^{[citation needed]}

Medically, it appears to relieve convulsion, inflammation, anxiety, and nausea, and to inhibit cancer cell growth.^[4] Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia.^[5]

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.^[6][7] It is also a neuroprotective antioxidant.^[8]

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.^[5] Further research has verified these results. Leweke et al., (2009) performed a double blind, 4 week, explorative study 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 schizophrenia. 'Both treatments were associated with a significant decrease of psychotic symptoms after 2 and 4 weeks as assessed by BPRS and PANSS. However, there was no statistical difference between both treatment groups. In contrast, cannabidiol induced significantly less side effects (EPS, increase in prolactin, weight gain) when compared to amisulpride'.^[9] The authors conclude cannabidiol revealed substantial antipsychotic properties in acute paranoid schizophirenia (Leweke et al., 2009). This led the authors to suggest the endocannabinoid system plays an adaptive role in the development of paranoid schizophirenia and that this research provides evidence that this mechanism may be a valuable target for 'antipsychotic treament strategies' .^[9]

Pharmacology

Cannabidiol has no affinity for CB₁ and CB₂ receptors but acts as an indirect antagonist of cannabinoid agonists.^[4] Recently it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen.^[10]

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."^[11] 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.^[6]

Chemistry

Cannabidiol is insoluble in water but soluble in organic solvents. At room temperature it is a colorless crystalline solid.^[12] In strongly basic medium and the presence of air it is oxidized to a quinone.^[13] Under acidic conditions it cyclizes to THC.^[14] The synthesis of cannabidiol has been accomplished by several research groups.^[15][16][17]

Legal Status

In Canada Cannabadiol is a Schedule 2 Drug, a category that encompasses quantities of cannabis less than 30 grams, and various related synthetic derivatives and preparations^[18].

See also

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

References

External links

• Erowid Compounds found in Cannabis sativa