:Cannabidivarin

{{Short description|Group of stereoisomers}}

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| verifiedrevid = 460016211

| IUPAC_name = 2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl)
cyclohex-2-enyl)-5-propylbenzene-1,3-diol

| image = Cannabidivarin.svg

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| image2 = Cannabidivarin molecule ball.png

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 24274-48-4

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| UNII = I198VBV98I

| ATC_prefix = none

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| ChEMBL = 2387742

| KEGG = C20217

| PubChem = 11601669

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| ChemSpiderID = 21106275

| C=19 | H=26 | O=2

| smiles = C=C(C)[C@H]2CCC(\C)=C/[C@@H]2c1c(O)cc(CCC)cc1O

| 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 cannabinoid found in Cannabis. It is a homolog (chemistry) of cannabidiol (CBD), with the side-chain shortened by two methylene bridges (CH₂ units).

Although cannabidivarin (CBDV) is usually a minor constituent of the cannabinoid profile, enhanced 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.{{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 }}{{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 = 966–975 | date = June 2004 | pmid = 21653452 | doi = 10.3732/ajb.91.6.966 | doi-access = free }}{{cite journal | vauthors = Merkus FW | title = Cannabivarin and tetrahydrocannabivarin, two new constituents of hashish | journal = Nature | volume = 232 | issue = 5312 | pages = 579–580 | date = August 1971 | pmid = 4937510 | doi = 10.1038/232579a0 | s2cid = 4219797 | bibcode = 1971Natur.232..579M }}

CBDV demonstrated anticonvulsant in rodent models in a single published study.{{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 }} It was identified for the first time in 1969 by Vollner et al.{{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 }}

Similarly to CBD, it has seven double bond isomers and 30 stereoisomers (see: Cannabidiol#Isomerism). It is not scheduled by Convention on Psychotropic Substances. It is being actively developed by GW Pharmaceuticals (as GWP42006){{cite web |url=https://www.gwpharm.com/about/news/gw-pharmaceuticals-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}} because of a demonstrated neurochemical pathway for previously observed anti-epileptic and anti-convulsive action.{{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 | pages = e214 | year = 2013 | pmid = 24282673 | pmc = 3840466 | doi = 10.7717/peerj.214 | doi-access = free }} GW has begun several Phase-2 trials for adult epilepsy,{{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 |access-date=November 10, 2015 }} for childhood epilepsy and for Prader-Willi Syndrome.{{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}}{{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}}