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Cannabidivarin: Difference between revisions

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{{Short description|Group of stereoisomers}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460016211
| IUPAC_name = 2-((1''S'',6''S'')-3-methyl-6-(prop-1-en-2-yl)<br />cyclohex-2-enyl)-5-propylbenzene-1,3-diol
| image = Cannabidivarin.svg
| image2 = Cannabidivarin molecule ball.png
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 24274-48-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I198VBV98I
| ATC_prefix = none
| ATC_suffix =
| PubChemChEMBL = 2387742
| KEGG = C20217
| PubChem = 11601669
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = noneDB14050
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106275
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<!--Chemical data-->
| C=19 | H=26 | O=2
| molecular_weight = 286.41 g/mol
| smiles = C=C(C)[C@H]2CCC(\C)=C/[C@@H]2c1c(O)cc(CCC)cc1O
| InChI = 1/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+/m1/s1
| InChIKey = REOZWEGFPHTFEI-CVEARBPZBI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+/m1/s1
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}}
 
'''Cannabidivarin''' ('''CBDV''', '''GWP42006''') is a non-intoxicating [[psychoactive substance|psychoactive]] [[cannabinoid]] found in ''[[Cannabis]]''. It is a [[homolog (chemistry)]] of [[cannabidiol]] (CBD), with the [[Side chain|side-chain]] shortened by two [[methylene bridge]]s (CH<sub>2</sub> units).
'''Cannabidivarin''' ('''CBDV''') is a non-[[psychoactive substance|psychoactive]] [[cannabinoid]] found in ''Cannabis''. It is a homolog of [[cannabidiol]] (CBD), with the [[Side chain|side-chain]] shortened by two [[methylene bridge]]s (CH<sub>2</sub> units). Plants with relatively high levels of CBDV have been reported in feral populations of ''C. indica'' ( = ''C. sativa'' ssp. ''indica'' var. ''kafiristanica'') from northwest India, and in hashish from Nepal.<ref>{{cite journal |vauthors=Turner CE, Cheng PC, Lewis GS, Russell MH, Sharma GK |year=1979 |title=Constituents of ''Cannabis sativa'' XV: Botanical and chemical profile of Indian variants |journal=Planta Medica |volume=37 |issue=3 |pages=217–25}}</ref><ref>{{cite journal |vauthors=Hillig KW, Mahlberg PG |title=A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae) |journal=American Journal of Botany |volume=91 |issue=6 |pages=966–75 |year=2004 |pmid=21653452 |doi=10.3732/ajb.91.6.966 }}</ref> CBDV has anticonvulsant effects.<ref>{{cite journal |vauthors=Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ |title=Cannabidivarin is anticonvulsant in mouse and rat |journal=British Journal of Pharmacology |volume=167 |issue=8 |pages=1629–42 |year=2012 |pmid=22970845 |pmc=3525866 |doi=10.1111/j.1476-5381.2012.02207.x }}</ref>▼
 
▲'''Cannabidivarin'''Although cannabidivarin ('''CBDV''') is usually a non-[[psychoactive substance|psychoactive]] [[cannabinoid]] found in ''Cannabis''. It is aminor homologconstituent of [[cannabidiol]] (CBD), with the [[Sidecannabinoid chain|side-chain]] shortened by two [[methylene bridge]]s (CH<sub>2</sub> units). Plants with relativelyprofile, highenhanced levels of CBDV have been reported in feral populations of ''C. indica'' ( = ''C. sativa'' ssp. ''indica'' var. ''kafiristanica'') from northwest [[India]], and in [[hashish]] from [[Nepal]].<ref>{{cite journal |vauthors=Turner CE, Cheng PC, Lewis GS, Russell MH, Sharma GK |year=1979 |title=Constituents of ''Cannabis sativa'' XV: Botanical and chemical profile of Indian variants |journal=Planta Medica |volume=37 |issue=3 |pages=217–25 | doi = 10.1055/s-0028-1097331|s2cid=83483599 }}</ref><ref name="HilligMahlberg">{{cite journal | vauthors = Hillig KW, Mahlberg PG | title = A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae) | journal = American Journal of Botany | volume = 91 | issue = 6 | pages =966–75 966–975 |year date = June 2004 | pmid = 21653452 | doi = 10.3732/ajb.91.6.966 | doi-access = free }}</ref> CBDV has anticonvulsant effects.<ref>{{cite journal | vauthors =Hill AJ,Merkus MercierFW MS,| Hilltitle TD,= GlynCannabivarin and SEtetrahydrocannabivarin, Jonestwo NA,new Yamasakiconstituents Y,of Futamurahashish T,| Duncanjournal M,= StottNature CG,| Stephensvolume GJ,= Williams232 CM,| Whalleyissue BJ= 5312 |title pages =Cannabidivarin is579–580 anticonvulsant| indate mouse= andAugust rat1971 |journal=British Journalpmid of= Pharmacology4937510 |volume=167 |issuedoi =8 |pages=1629–4210.1038/232579a0 |year s2cid =2012 4219797 |pmid=22970845 |pmcbibcode =3525866 |doi=10.1111/j.1476-53811971Natur.2012232.02207.x579M }}</ref>
Similarly to CBD, it has 7 double bond isomers and 30 stereoisomers (see: [[Cannabidiol#Double bond isomers and their stereoisomers]]). It is not scheduled by [[Convention on Psychotropic Substances]]. It is being actively developed by [[GW Pharmaceuticals]]<ref>http://www.gwpharm.com/therapeutic-areas.aspx{{full}}</ref> (as GWP42006)because of a demonstrated neurochemical pathway for previously-observed anti-epileptic and anti-convulsive action.<ref>{{cite journal |vauthors=Amada N, Yamasaki Y, Williams CM, Whalley BJ |title=Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression |journal=Peerj |volume=1 |issue= |pages=e214 |year=2013 |pmid=24282673 |pmc=3840466 |doi=10.7717/peerj.214 }}</ref> GW has begun a phase 2 trial for adult epilepsy.<ref>{{cite press release |title=GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy |publisher=GW Pharmaceuticals |date=May 6, 2015 |url=http://globenewswire.com/news-release/2015/05/06/732705/10132893/en/GW-Pharmaceuticals-Initiates-Phase-2-Clinical-Study-of-Cannabidivarin-CBDV-in-Epilepsy.html |accessdate=November 10, 2015 }}</ref>▼
 
CBDV demonstrated anticonvulsant in rodent models in a single published study.<ref>{{cite journal | vauthors = Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ | display-authors = 6 | title = Cannabidivarin is anticonvulsant in mouse and rat | journal = British Journal of Pharmacology | volume = 167 | issue = 8 | pages = 1629–1642 | date = December 2012 | pmid = 22970845 | pmc = 3525866 | doi = 10.1111/j.1476-5381.2012.02207.x }}</ref> It was identified for the first time in 1969 by Vollner et al.<ref>{{cite journal | vauthors = Vollner L, Bieniek D, Korte F | title = [Hashish. XX. Cannabidivarin, a new hashish constituent] | journal = Tetrahedron Letters | volume = 10 | issue = 3 | pages = 145–147 | date = January 1969 | pmid = 5778489 | doi = 10.1016/S0040-4039(01)87494-3 }}</ref>
 
▲Similarly to CBD, it has 7seven double bond isomers and 30 stereoisomers (see: [[Cannabidiol#Double bond isomers and their stereoisomersIsomerism]]). It is not scheduled by [[Convention on Psychotropic Substances]]. It is being actively developed by [[GW Pharmaceuticals]] (as GWP42006)<ref name="GWPharm18">http{{cite web |url=https://www.gwpharm.com/therapeuticabout/news/gw-areas.aspx{{fullpharmaceuticals-announces-preliminary-results-phase-2a-study-its-pipeline-compound |title=GW Pharmaceuticals Announces Preliminary Results of Phase 2a Study for its Pipeline Compound GWP42006 |publisher=GW Pharmaceuticals |date=21 February 2018 |access-date=28 May 2019}}</ref> (as GWP42006)because of a demonstrated neurochemical pathway for previously- observed anti-epileptic and anti-convulsive action.<ref>{{cite journal | vauthors = Amada N, Yamasaki Y, Williams CM, Whalley BJ | title = Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression | journal =Peerj PeerJ | volume = 1 |issue= |pages = e214 | year = 2013 | pmid = 24282673 | pmc = 3840466 | doi = 10.7717/peerj.214 | doi-access = free }}</ref> GW has begun a phaseseveral Phase-2 trialtrials for adult [[epilepsy.]],<ref>{{cite press release |title=GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy |publisher=GW Pharmaceuticals |date=May 6, 2015 |url=http://globenewswire.com/news-release/2015/05/06/732705/10132893/en/GW-Pharmaceuticals-Initiates-Phase-2-Clinical-Study-of-Cannabidivarin-CBDV-in-Epilepsy.html |accessdateaccess-date=November 10, 2015 }}</ref> for childhood epilepsy and for Prader-Willi Syndrome.<ref>{{Cite web|url = http://ir.gwpharm.com/releasedetail.cfm?ReleaseID=938568|title = GW Pharma Press release|archive-url = https://web.archive.org/web/20151121025630/http://ir.gwpharm.com/releasedetail.cfm?ReleaseID=938568|archive-date = 2015-11-21|url-status = dead}}</ref><ref>{{Cite web|url =http://www.health.nsw.gov.au/cannabis/Documents/medicial-cannabis-practitioners.pdf|title =NSW advice to practitioners on Medical Cannabis trials|archive-url =https://web.archive.org/web/20151121020442/http://www.health.nsw.gov.au/cannabis/Documents/medicial-cannabis-practitioners.pdf|archive-date =2015-11-21|url-status =dead}}</ref>
 
== See also ==
* [[List of investigational analgesics]]
* [[Cannabinoids]]
* [[Cannabis]]
* [[Medical marijuana]]
 
== References ==
{{Reflist|2}}
{{Refimprove|date=October 2009}}
 
== External links ==
* [httphttps://www.erowid.org/plants/cannabis/cannabis_info2.shtml Erowid] Compounds found in ''Cannabis sativa''
* [https://pubchem.ncbi.nlm.nih.gov/compound/Cannabidivarin Cannabidivarin]
 
{{Cannabinoids}}
{{Transient receptor potential channel modulators}}
 
[[Category:CannabinoidsPhytocannabinoids]]
[[Category:Natural phenols]]
[[Category:Resorcinols]]
[[Category:Cyclohexenes]]
 
[[Category:Transient receptor potential channel modulators]]
 
{{cannabinoid-stub}}
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