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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
Characterization of palmitoylethanolamide transport in mouse Neuro-2a neuroblastoma and rat RBL-2H3 basophilic leukaemia cells: comparison with anandamide.
2001 Apr
Cannabinoid-induced alterations in brain disposition of drugs of abuse.
2001 Jun 1
Alcohol and marijuana: effects on epilepsy and use by patients with epilepsy.
2001 Oct
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.
2001 Oct
Assessment of the role of CB1 receptors in cannabinoid anticonvulsant effects.
2001 Sep 28
CB(1) receptor antagonist SR141716A inhibits Ca(2+)-induced relaxation in CB(1) receptor-deficient mice.
2002 Feb
Cannabinol enhancement of interleukin-2 (IL-2) expression by T cells is associated with an increase in IL-2 distal nuclear factor of activated T cell activity.
2002 Feb
DNA fingerprinting of Cannabis sativa using inter-simple sequence repeat (ISSR) amplification.
2002 Jan
The potent emetogenic effects of the endocannabinoid, 2-AG (2-arachidonoylglycerol) are blocked by delta(9)-tetrahydrocannabinol and other cannnabinoids.
2002 Jan
Determination of cannabinoids in hair using high-pH* non-aqueous electrolytes and electrochemical detection. Some aspects of sensitivity and selectivity.
2002 Jan 4
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