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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

PubMed

PubMed

TitleDatePubMed
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
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
Patents

Patents

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