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Cannabidivarin

From Wikipedia, the free encyclopedia
Group of stereoisomers

Pharmaceutical compound
Cannabidivarin
Clinical data
ATC code
  • none
Identifiers
  • 2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl)
    cyclohex-2-enyl)-5-propylbenzene-1,3-diol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.236.933Edit this at Wikidata
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
  • C=C(C)[C@H]2CCC(\C)=C/[C@@H]2c1c(O)cc(CCC)cc1O
  • 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 checkY
  • Key:REOZWEGFPHTFEI-CVEARBPZSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cannabidivarin (CBDV,GWP42006) is a non-intoxicatingpsychoactivecannabinoid found inCannabis. It is ahomolog (chemistry) ofcannabidiol (CBD), with theside-chain shortened by twomethylene 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 ofC. indica ( =C. sativa ssp.indica var.kafiristanica) from northwestIndia, and inhashish fromNepal.[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 byConvention on Psychotropic Substances. It is being actively developed byGW 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 adultepilepsy,[8] for childhood epilepsy and for Prader-Willi Syndrome.[9][10]

See also

[edit]

References

[edit]
  1. ^Turner CE, Cheng PC, Lewis GS, Russell MH, Sharma GK (1979). "Constituents ofCannabis 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. Retrieved28 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. RetrievedNovember 10, 2015.
  9. ^"GW Pharma Press release". Archived fromthe original on 2015-11-21.
  10. ^"NSW advice to practitioners on Medical Cannabis trials"(PDF). Archived fromthe original(PDF) on 2015-11-21.

External links

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