Cannabidivarin

Cannabidivarin (CBDV, GWP42006) is a non-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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.236.933
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
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][4]

CBDV has anticonvulsant effects.[5] It was identified for the first time in 1969 by Vollner et al.[6]

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)[7] because of a demonstrated neurochemical pathway for previously observed anti-epileptic and anti-convulsive action.[8] GW has begun a phase 2 trial for adult epilepsy,[9] and is to begin trials of this CBDV product in children in 2016 in Australia.[10][11]

See also

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.
  2. Hillig KW, Mahlberg PG (2004). "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany. 91 (6): 966–75. doi:10.3732/ajb.91.6.966. PMID 21653452.
  3. Hillig KW, Mahlberg PG (June 2004). "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany. 91 (6): 966–75. doi:10.3732/ajb.91.6.966. PMID 21653452.
  4. Merkus FW (August 1971). "Cannabivarin and tetrahydrocannabivarin, two new constituents of hashish". Nature. 232 (5312): 579–80. Bibcode:1971Natur.232..579M. doi:10.1038/232579a0. PMID 4937510. S2CID 4219797.
  5. Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ (2012). "Cannabidivarin is anticonvulsant in mouse and rat". British Journal of Pharmacology. 167 (8): 1629–42. doi:10.1111/j.1476-5381.2012.02207.x. PMC 3525866. PMID 22970845.
  6. Vollner, L.; Bieniek, D.; Korte, F. (1969-01-01). "Haschisch XX11XIX. Mitteillung: F. von Spulak, U. Claussen, H.-W. Fehlhaber und F. Korte, Tetrahedron 24, 5379 (1968).: Cannabidivarin, ein neuer Haschisch-Inhaltsstoff". Tetrahedron Letters. 10 (3): 145–147. doi:10.1016/S0040-4039(01)87494-3. ISSN 0040-4039. PMID 5778489.
  7. "GW Pharmaceuticals Announces Preliminary Results of Phase 2a Study for its Pipeline Compound GWP42006". GW Pharmaceuticals. 21 February 2018. Retrieved 28 May 2019.
  8. 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.
  9. "GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy" (Press release). GW Pharmaceuticals. May 6, 2015. Retrieved November 10, 2015.
  10. "GW Pharma Press release". Archived from the original on 2015-11-21.
  11. "NSW advice to practitioners on Medical Cannabis trials" (PDF). Archived from the original (PDF) on 2015-11-21.


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