Chemistry:Cannabidivarin

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Short description: Group of stereoisomers
Cannabidivarin
Cannabidivarin.svg
Cannabidivarin molecule ball.png
Clinical data
ATC code
  • none
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CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
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Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
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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.[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). 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

References

  1. "Constituents of Cannabis sativa XV: Botanical and chemical profile of Indian variants". Planta Medica 37 (3): 217–25. 1979. doi:10.1055/s-0028-1097331. 
  2. "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany 91 (6): 966–975. June 2004. doi:10.3732/ajb.91.6.966. PMID 21653452. 
  3. "Cannabivarin and tetrahydrocannabivarin, two new constituents of hashish". Nature 232 (5312): 579–580. August 1971. doi:10.1038/232579a0. PMID 4937510. Bibcode1971Natur.232..579M. 
  4. "Cannabidivarin is anticonvulsant in mouse and rat". British Journal of Pharmacology 167 (8): 1629–1642. December 2012. doi:10.1111/j.1476-5381.2012.02207.x. PMID 22970845. 
  5. "[Hashish. XX. Cannabidivarin, a new hashish constituent]". Tetrahedron Letters 10 (3): 145–147. January 1969. 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. https://www.gwpharm.com/about/news/gw-pharmaceuticals-announces-preliminary-results-phase-2a-study-its-pipeline-compound. 
  7. "Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression". PeerJ 1: e214. 2013. doi:10.7717/peerj.214. 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". http://ir.gwpharm.com/releasedetail.cfm?ReleaseID=938568. 
  10. "NSW advice to practitioners on Medical Cannabis trials". http://www.health.nsw.gov.au/cannabis/Documents/medicial-cannabis-practitioners.pdf. 

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