Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:35:28 UTC |
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Updated at | 2020-11-18 16:35:09 UTC |
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CannabisDB ID | CDB000015 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Cannabidivarin |
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Description | Cannabidivarin (CBDV) is a non-psychoactive cannabinoid found within medical Cannabis. It is one of over 100 cannabinoids identified from the Cannabis plants that can modulate the physiological activity of cannabis, or marijuana (PMID: 23408483 ). CBDV is the C3 analogue of cannabidiol (CBD). Notably, both cannabidiol and CBDV have demonstrated anticonvulsant activity in animal and human models with promising clinical trial results (PMID: 22970845 ; PMID: 25029033 ; PMID: 29290836 ; PMID: 29588939 ). Other cannabinoids with demonstrated anti-epileptic activity include Tetrahydrocannabivarin (THCV) and Δ9-tetrahydrocannabinolic acid. While the primary components of cannabis, CBD and THC, have been shown to modulate many of their physiological effects through their binding to the cannabinoid-1 (CB1) and cannabinoid-2 (CB2) receptors, the anticonvulsant cannabinoids do not interact with CB1 and CB2. 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. TRPV1 is a member 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 transient receptor potential ankyrin 1 (TRPA1) channels (PMID 25029033 ; PMID: 29842819 ; PMID: 21175579 ). 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-α, the primary enzyme responsible for the synthesis of the endocannabinoid, 2-arachidonoylglycerol (2-AG) (PMID: 24282673 ; PMID: 14610053 ). The clinical implications of this are unclear however, as this interaction has not been shown to affect CBDV's anticonvulsant activity. CBDV is being actively developed by GW Pharmaceuticals as the experimental compound GWP42006 as it has "shown the ability to treat seizures in pre-clinical models of epilepsy with significantly fewer side effects than currently approved anti-epileptic drugs". Unfortunately, as of February 2018, GW Pharmaceuticals announced that their Phase 2a placebo-controlled study of CBDV for focal seizure did not reach its primary endpoints. They will continue to study its use in epilepsy, however, and are expanding their investigations to include its potential use in Autism Spectrum Disorder, Rett syndrome and Fragile X among others. 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. |
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Structure | |
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Synonyms | Value | Source |
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CBDV | Kegg | CBDV Compound | MeSH |
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Chemical Formula | C19H26O2 |
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Average Molecular Weight | 286.42 |
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Monoisotopic Molecular Weight | 286.1933 |
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IUPAC Name | 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol |
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Traditional Name | 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol |
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CAS Registry Number | 24274-48-4 |
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SMILES | CCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 |
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InChI Identifier | 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 |
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InChI Key | REOZWEGFPHTFEI-JKSUJKDBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Aromatic monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Aromatic monoterpenoid
- Phenylpropane
- Resorcinol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Not Available | Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | Not Available | Not Available |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Cannabidivarin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cannabidivarin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum |
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NMR | Not Available |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | |
Sn1-specific diacylglycerol lipase alpha | DAGLA | 11q12.2 | Q9Y4D2 | details |
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Transporters | |
Transient receptor potential cation channel subfamily V member 1 | TRPV1 | 17p13.2 | Q8NER1 | details | Transient receptor potential cation channel subfamily V member 2 | TRPV2 | 17p11.2 | Q9Y5S1 | details | Transient receptor potential cation channel subfamily A member 1 | TRPA1 | 8q13 | O75762 | details |
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Metal Bindings | Not Available |
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Receptors | |
Transient receptor potential cation channel subfamily V member 1 | TRPV1 | 17p13.2 | Q8NER1 | details | Transient receptor potential cation channel subfamily V member 2 | TRPV2 | 17p11.2 | Q9Y5S1 | details | Transient receptor potential cation channel subfamily A member 1 | TRPA1 | 8q13 | O75762 | details |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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Alien Dawg | Detected and Quantified | 0.000416 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.000608 mg/g dry wt | | details | Island Honey | Detected and Quantified | 0.000508 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.00044 mg/g dry wt | | details | Sensi Star | Detected and Quantified | 0.000491 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.000606 mg/g dry wt | | details |
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External Links |
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HMDB ID | Not Available |
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DrugBank ID | DB14050 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | C20217 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Cannabidivarin |
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METLIN ID | Not Available |
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PubChem Compound | 11601669 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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References |
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General References | - Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ: Cannabidivarin is anticonvulsant in mouse and rat. Br J Pharmacol. 2012 Dec;167(8):1629-42. doi: 10.1111/j.1476-5381.2012.02207.x. [PubMed:22970845 ]
- Iannotti FA, Hill CL, Leo A, Alhusaini A, Soubrane C, Mazzarella E, Russo E, Whalley BJ, Di Marzo V, Stephens GJ: Nonpsychotropic plant cannabinoids, cannabidivarin (CBDV) and cannabidiol (CBD), activate and desensitize transient receptor potential vanilloid 1 (TRPV1) channels in vitro: potential for the treatment of neuronal hyperexcitability. ACS Chem Neurosci. 2014 Nov 19;5(11):1131-41. doi: 10.1021/cn5000524. Epub 2014 Jul 29. [PubMed:25029033 ]
- Capasso A: Do Cannabinoids Confer Neuroprotection Against Epilepsy? An Overview. Open Neurol J. 2017 Dec 18;11:61-73. doi: 10.2174/1874205X01711010061. eCollection 2017. [PubMed:29290836 ]
- Morano A, Cifelli P, Nencini P, Antonilli L, Fattouch J, Ruffolo G, Roseti C, Aronica E, Limatola C, Di Bonaventura C, Palma E, Giallonardo AT: Cannabis in epilepsy: From clinical practice to basic research focusing on the possible role of cannabidivarin. Epilepsia Open. 2016 Sep 19;1(3-4):145-151. doi: 10.1002/epi4.12015. eCollection 2016 Dec. [PubMed:29588939 ]
- Ruzic Zecevic D, Folic M, Tantoush Z, Radovanovic M, Babic G, Jankovic SM: Investigational cannabinoids in seizure disorders, what have we learned thus far? Expert Opin Investig Drugs. 2018 Jun;27(6):535-541. doi: 10.1080/13543784.2018.1482275. Epub 2018 Jun 6. [PubMed:29842819 ]
- De Petrocellis L, Ligresti A, Moriello AS, Allara M, Bisogno T, Petrosino S, Stott CG, Di Marzo V: Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol. 2011 Aug;163(7):1479-94. doi: 10.1111/j.1476-5381.2010.01166.x. [PubMed:21175579 ]
- Amada N, Yamasaki Y, Williams CM, Whalley BJ: Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression. PeerJ. 2013 Nov 21;1:e214. doi: 10.7717/peerj.214. eCollection 2013. [PubMed:24282673 ]
- Bisogno T, Howell F, Williams G, Minassi A, Cascio MG, Ligresti A, Matias I, Schiano-Moriello A, Paul P, Williams EJ, Gangadharan U, Hobbs C, Di Marzo V, Doherty P: Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J Cell Biol. 2003 Nov 10;163(3):463-8. doi: 10.1083/jcb.200305129. [PubMed:14610053 ]
- Sharma P, Murthy P, Bharath MM: Chemistry, metabolism, and toxicology of cannabis: clinical implications. Iran J Psychiatry. 2012 Fall;7(4):149-56. [PubMed:23408483 ]
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