Cannabidivarin

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).

Cannabidivarin

Clinical data
ATC code	none
Identifiers
IUPAC name 2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl) cyclohex-2-enyl)-5-propylbenzene-1,3-diol
CAS Number	24274-48-4 N
PubChem CID	11601669
DrugBank	DB14050 N
ChemSpider	21106275 Y
UNII	I198VBV98I
KEGG	C20217
ChEMBL	ChEMBL2387742
CompTox Dashboard (EPA)	DTXSID70893921
ECHA InfoCard	100.236.933
Chemical and physical data
Formula	C19H26O2
Molar mass	286.415 g·mol−1
3D model (JSmol)	Interactive image
SMILES C=C(C)[C@H]2CCC(\C)=C/[C@@H]2c1c(O)cc(CCC)cc1O
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+/m1/s1 Y Key:REOZWEGFPHTFEI-CVEARBPZSA-N Y
NY (what is this?)  (verify)

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.^[1][2][3]

CBDV demonstrated anticonvulsant in rodent models in a single published study.^[4] It was identified for the first time in 1969 by Vollner et al.^[5]

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)^[6] because of a demonstrated neurochemical pathway for previously observed anti-epileptic and anti-convulsive action.^[7] GW has begun several Phase-2 trials for adult epilepsy,^[8] for childhood epilepsy and for Prader-Willi Syndrome.^[9][10]

See also

• List of investigational analgesics

References

1. Turner CE, Cheng PC, Lewis GS, Russell MH, Sharma GK (1979). "Constituents of Cannabis sativa XV: Botanical and chemical profile of Indian variants". Planta Medica. 37 (3): 217–25. doi:10.1055/s-0028-1097331. S2CID 83483599.
2. Hillig KW, Mahlberg PG (June 2004). "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany. 91 (6): 966–975. doi:10.3732/ajb.91.6.966. PMID 21653452.
3. Merkus FW (August 1971). "Cannabivarin and tetrahydrocannabivarin, two new constituents of hashish". Nature. 232 (5312): 579–580. Bibcode:1971Natur.232..579M. doi:10.1038/232579a0. PMID 4937510. S2CID 4219797.
4. Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, et al. (December 2012). "Cannabidivarin is anticonvulsant in mouse and rat". British Journal of Pharmacology. 167 (8): 1629–1642. doi:10.1111/j.1476-5381.2012.02207.x. PMC 3525866. PMID 22970845.
5. Vollner L, Bieniek D, Korte F (January 1969). "[Hashish. XX. Cannabidivarin, a new hashish constituent]". Tetrahedron Letters. 10 (3): 145–147. doi:10.1016/S0040-4039(01)87494-3. PMID 5778489.
6. "GW Pharmaceuticals Announces Preliminary Results of Phase 2a Study for its Pipeline Compound GWP42006". GW Pharmaceuticals. 21 February 2018. Retrieved 28 May 2019.
7. Amada N, Yamasaki Y, Williams CM, Whalley BJ (2013). "Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression". PeerJ. 1: e214. doi:10.7717/peerj.214. PMC 3840466. PMID 24282673.
8. "GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy" (Press release). GW Pharmaceuticals. May 6, 2015. Retrieved November 10, 2015.
9. "GW Pharma Press release". Archived from the original on 2015-11-21.
10. "NSW advice to practitioners on Medical Cannabis trials" (PDF). Archived from the original (PDF) on 2015-11-21.

External links

• Erowid Compounds found in Cannabis sativa
• Cannabidivarin