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Cannabidivarin

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Chemistry

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Also known as: Cannabidivarol, 24274-48-4, Cbdv, Cbd-v, Gwp42006, I198vbv98i

Molecular Formula

C₁₉H₂₆O₂

Molecular Weight

286.4 g/mol

InChI Key

REOZWEGFPHTFEI-JKSUJKDBSA-N

FDA UNII

I198VBV98I

2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol is a natural product found in Cannabis sativa with data available.

1 2D Structure

Cannabidivarin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol

2.1.2 InChI

InChI=1S/C19H26O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h9-11,15-16,20-21H,2,5-8H2,1,3-4H3/t15-,16+/m0/s1

2.1.3 InChI Key

REOZWEGFPHTFEI-JKSUJKDBSA-N

2.1.4 Canonical SMILES

CCCC1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O

2.1.5 Isomeric SMILES

CCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O

2.2 Other Identifiers

2.2.1 UNII

I198VBV98I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cbdv Compound

2.3.2 Depositor-Supplied Synonyms

1. Cannabidivarol

2. 24274-48-4

3. Cbdv

4. Cbd-v

5. Gwp42006

6. I198vbv98i

7. Gwp-42006

8. 2-[(1r,6r)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol

9. Cannabidivarin (cbdv)

10. (1'r,2'r)-5'-methyl-2'-(prop-1-en-2-yl)-4-propyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol

11. Cannabidivarine

12. (1r-trans)-2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-propyl-1,3-benzenediol

13. Unii-i198vbv98i

14. Schembl2759238

15. Chembl2387742

16. Chebi:182159

17. Dtxsid801019159

18. Cannabidivarin [nflis-drug]

19. Zinc5844413

20. Bdbm50532215

21. Akos030242161

22. Db14050

23. 1,3-benzenediol, 2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-propyl-, (1r-trans)-

24. Ac-34111

25. Bc175204

26. C20217

27. Cannabidivarin (cbdv) 100 Microg/ml In Methanol

28. Cannabidivarin (cbdv) 1000 Microg/ml In Methanol

29. Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-propyl-

30. 1,3-benzenediol, 2-((1r,6r)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-propyl-

31. 2-((1r,6r)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl)-5-propylbenzene-1,3-diol

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₆O₂
Molecular Weight	286.4 g/mol
XLogP3	5.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	286.193280068 g/mol
Monoisotopic Mass	286.193280068 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	386
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Cannabidivarin does not currently have any FDA or Health Canada approved indications, however in October 2017 CBDV was given orphan designation by the European Medicines Agency for use in Rett Syndrome and again in February 2018 for treatment of Fragile X Syndrome.

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Absorption

Like 9-THC, CBDV has low water solubility and poor oral bioavailability (~6% in humans), making oral administration an unfavourable method of delivery. Despite this, CBDV has relatively rapid absorption with peak concentrations seen around 2 h after oral administration in animal pharmacokinetic studies. Orally administered CBDV in mice was found to have a plasma Cmax of 0.47ug/mL and Tmax of 30 minutes, and a brain Cmax of 0.94ug/mL and Tmax of 60 minutes.

Volume of Distribution

Due to its lipophilicity, CBDV has been shown to cross the blood brain barrier.

5.2 Metabolism/Metabolites

Significant first-pass metabolism by the liver results in erratic absorption from the GI tract, low bioavailability, and unreliable pharmacokinetics.

5.3 Biological Half-Life

Orally administered CBDV in mice was found to have a plasma elimination half life of 222 minutes, and a brain elimination half life of 204 minutes.

5.4 Mechanism of Action

The anti-epileptic activity of CBD and CBDV is thought to be modulated by their effects on transient receptor potential cation channel subfamily V member 1 (TRPV1), also known as the capsaicin receptor, which is part of a large family of ion channels that are involved in the onset and progression of several types of epilepsy. CBD and CBDV have been shown to dose-dependently activate and then desensitize TRPV1 as well as TRPV2 and TRPA1 channels. Desensitization of these ion channels is a potential mechanism by which these molecules cause a reduction of neuronal hyperexcitability that contributes to epileptic activity and seizures. CBDV has also been shown to inhibit the activity of diacylglycerol (DAG) lipase-, the primary synthetic enzyme of the endocannabinoid, 2-arachidonoylglycerol (2-AG). The clinical implications of this are unclear however, as this interaction has not been shown to affect CBDV's anticonvulsant activity.

Drugs in Development