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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O2
Molecular Weight 314.4617
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CANNABIDIOL

SMILES

CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1

InChI

InChIKey=QHMBSVQNZZTUGM-ZWKOTPCHSA-N
InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H30O2
Molecular Weight 314.4617
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cannabidiol is the major nonpsychoactive ingredient in cannabis. Cannabidiol demonstrates a range of effects that may be therapeutically useful, including anti-seizure, antioxidant, neuroprotective, anti-inflammatory, analgesic, anti-tumor, anti-psychotic, and anti-anxiety properties. Exact mechanism of action of cannabidiol is not known, but may include effects on the orphan G-protein-coupled receptor GPR55; the transient receptor potential of vanilloid type-1 channel; the 5-HT1a receptor; and the α3 glycine receptors. GW Pharmaceuticals successfully developed the world’s first prescription medicine derived from the cannabis plant, Sativex® (buccal spray containing delta-9-tetrahydrocannabinol and cannabidiol) now approved in over 29 countries outside of the United States for the treatment of spasticity due to Multiple Sclerosis. GW Pharmaceuticals is developing Epidiolex® (a liquid formulation of pure plant-derived cannabidiol) for certain rare and severe early-onset, drug-resistant epilepsy syndromes.

CNS Activity

Originator

Approval Year

PMID

PMID

TitleDatePMID
Medicinal cannabis: is delta9-tetrahydrocannabinol necessary for all its effects?
2003 Dec
Gamma-irradiation enhances apoptosis induced by cannabidiol, a non-psychotropic cannabinoid, in cultured HL-60 myeloblastic leukemia cells.
2003 Oct
Neuroprotective effect of cannabidiol, a non-psychoactive component from Cannabis sativa, on beta-amyloid-induced toxicity in PC12 cells.
2004 Apr
Atypical cannabinoid stimulates endothelial cell migration via a Gi/Go-coupled receptor distinct from CB1, CB2 or EDG-1.
2004 Apr 5
Do cannabis-based medicinal extracts have general or specific effects on symptoms in multiple sclerosis? A double-blind, randomized, placebo-controlled study on 160 patients.
2004 Aug
An open-label pilot study of cannabis-based extracts for bladder dysfunction in advanced multiple sclerosis.
2004 Aug
Efficacy, safety and tolerability of an orally administered cannabis extract in the treatment of spasticity in patients with multiple sclerosis: a randomized, double-blind, placebo-controlled, crossover study.
2004 Aug
Pain reduction and lack of psychotropic effects with ajulemic acid: comment on the article by Sumariwalla et al.
2004 Dec
Differential effects of THC- or CBD-rich cannabis extracts on working memory in rats.
2004 Dec
Efficacy of two cannabis based medicinal extracts for relief of central neuropathic pain from brachial plexus avulsion: results of a randomised controlled trial.
2004 Dec
(+)-Cannabidiol analogues which bind cannabinoid receptors but exert peripheral activity only.
2004 Dec 15
Effects of coadministration of cannabinoids and morphine on nociceptive behaviour, brain monoamines and HPA axis activity in a rat model of persistent pain.
2004 Feb
Medicinal cannabis extracts for the treatment of multiple sclerosis.
2004 Jul
A comparative analysis of the potential of cannabinoids and ondansetron to suppress cisplatin-induced emesis in the Suncus murinus (house musk shrew).
2004 Jul
Synthesis and antitumor activity of quinonoid derivatives of cannabinoids.
2004 Jul 15
Effect of Delta-9-tetrahydrocannabinol and cannabidiol on nocturnal sleep and early-morning behavior in young adults.
2004 Jun
Cannabidiol increases Fos expression in the nucleus accumbens but not in the dorsal striatum.
2004 Jun 18
Human skin permeation of Delta8-tetrahydrocannabinol, cannabidiol and cannabinol.
2004 Mar
A novel synthetic, nonpsychoactive cannabinoid acid (HU-320) with antiinflammatory properties in murine collagen-induced arthritis.
2004 Mar
Oral anti-inflammatory activity of cannabidiol, a non-psychoactive constituent of cannabis, in acute carrageenan-induced inflammation in the rat paw.
2004 Mar
6"-Azidohex-2"-yne-cannabidiol: a potential neutral, competitive cannabinoid CB1 receptor antagonist.
2004 Mar 8
Initial experiences with medicinal extracts of cannabis for chronic pain: results from 34 'N of 1' studies.
2004 May
Cannabidiol lacks the vanilloid VR1-mediated vasorespiratory effects of capsaicin and anandamide in anaesthetised rats.
2004 May 3
Determination of cannabinoids in cannabis products using liquid chromatography-ion trap mass spectrometry.
2004 Nov 26
NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa.
2004 Nov-Dec
Cannabidiol prevents infarction via the non-CB1 cannabinoid receptor mechanism.
2004 Oct 25
Cannabinoids in hair: strategy to prove marijuana/hashish consumption.
2004 Oct 29
Cannabis (marijuana) contamination of United States and foreign paper currency.
2004 Sep
Vanilloid TRPV1 receptor mediates the antihyperalgesic effect of the nonpsychoactive cannabinoid, cannabidiol, in a rat model of acute inflammation.
2004 Sep
Effect of low doses of delta9-tetrahydrocannabinol and cannabidiol on the extinction of cocaine-induced and amphetamine-induced conditioned place preference learning in rats.
2004 Sep
Cannabidiol inhibits human glioma cell migration through a cannabinoid receptor-independent mechanism.
2005 Apr
Cannabidiol inhibits the hyperlocomotion induced by psychotomimetic drugs in mice.
2005 Apr 11
Comparison of cannabidiol, antioxidants, and diuretics in reversing binge ethanol-induced neurotoxicity.
2005 Aug
Gene ancestry of the cannabinoid receptor family.
2005 Dec
The nonpsychoactive component of marijuana cannabidiol modulates chemotaxis and IL-10 and IL-12 production of murine macrophages both in vivo and in vitro.
2005 Feb
Marijuana extracts possess the effects like the endocrine disrupting chemicals.
2005 Jan 31
A rapid and simple procedure for the determination of cannabinoids in hemp food products by gas chromatography-mass spectrometry.
2005 Jan 4
Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L.
2005 Jan-Feb
The use of cannabinoids in multiple sclerosis.
2005 Jul
Evidence that (-)-7-hydroxy-4'-dimethylheptyl-cannabidiol activates a non-CB(1), non-CB(2), non-TRPV1 target in the mouse vas deferens.
2005 Jun
Peripheral, but not central effects of cannabidiol derivatives: mediation by CB(1) and unidentified receptors.
2005 Jun
CB1 cannabinoid receptor-mediated modulation of food intake in mice.
2005 Jun
Cannabinoids provide neuroprotection against 6-hydroxydopamine toxicity in vivo and in vitro: relevance to Parkinson's disease.
2005 Jun-Jul
Effect of cannabis use in human brain activity.
2005 Mar
Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors.
2005 Mar 21
Cannabinoids in bipolar affective disorder: a review and discussion of their therapeutic potential.
2005 May
Cannabidiol prevents cerebral infarction via a serotonergic 5-hydroxytryptamine1A receptor-dependent mechanism.
2005 May
Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids.
2005 Sep
Effects of RM-beta-CD on sublingual bioavailability of Delta9-tetrahydrocannabinol in rabbits.
2005 Sep
Cannabidiol reverses MK-801-induced disruption of prepulse inhibition in mice.
2006 Apr
Patent

Sample Use Guides

In Vivo Use Guide
SATIVEX® is provided as a buccal spray in a 5.5 ml vial, with each 100 microlitre spray providing 2.7 mg delta-9-tetrahydrocannabinol (THC) and 2.5 mg cannabidiol (CBD). In patients with multiple sclerosis, the median daily dosage of SATIVEX® in the extension phase of the 4-week clinical trial was 5 sprays per day. The majority of patients required 12 sprays or less; dosage should be adjusted as needed and tolerated. There is limited experience with doses higher than 12 sprays per day. Some patients may require and may tolerate a higher number of sprays. In patients with pain in cancer, the median daily dosage of SATIVEX® was 8 actuations (sprays).
Route of Administration: Topical
In Vitro Use Guide
in vitro pre-treatment of Human Gingival Mesenchymal Stem Cells with 5 uM Cannabidiol (CBD) can influence their expression profile
Substance Class Chemical
Created
by admin
on Tue Mar 06 17:16:37 UTC 2018
Edited
by admin
on Tue Mar 06 17:16:37 UTC 2018
Record UNII
19GBJ60SN5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CANNABIDIOL
INCI   INN   MART.   MI   USAN   WHO-DD  
USAN   INN   INCI  
Official Name English
CANNABIDIOL [USAN]
Common Name English
.DELTA.1(2)-TRANS-CANNABIDIOL
Common Name English
EPIDIOLEX
Brand Name English
CANNABIDIOL [MART.]
Common Name English
2-((1R,6R)-3-METHYL-6-(PROP-1-EN-2-YL)CYCLOHEX-2-EN-1-YL)- 5-PENTYLBENZENE-1,3-DIOL
Systematic Name English
2-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)CYCLOHEX-2-ENYL)-5-PENTYLBENZENE-1,3-DIOL
Systematic Name English
CANNABIDIOL [INCI]
Common Name English
GWP-42003
Code English
CANNABIDIOL [MI]
Common Name English
CBD
Common Name English
1,3-BENZENEDIOL, 2-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL)-5-PENTYL-
Systematic Name English
GWP-42003-P
Code English
CANNABIDIOL [INN]
Common Name English
CANNABIDIOL [WHO-DD]
Common Name English
GWP42003
Code English
GWP42003-P
Code English
Classification Tree Code System Code
WHO-ATC N02BG10
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
Code System Code Type Description
ChEMBL
CHEMBL190461
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
EVMPD
SUB26600
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
NCI_THESAURUS
C118452
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
WIKIPEDIA
CANNABIDIOL
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
INN
10423
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
CAS
13956-29-1
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
PUBCHEM
644019
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY SWITZERF
MESH
D002185
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY
MERCK INDEX
M3020
Created by admin on Tue Mar 06 17:16:37 UTC 2018 , Edited by admin on Tue Mar 06 17:16:37 UTC 2018
PRIMARY Merck Index
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
Cannabidiol Class | Anxiolytic Antipsychotic | Analgesic | Anti-inflammatory | Antioxydant | Antispasmodic
Related Record Type Details
ACTIVE MOIETY