Cannabidivarin

Last updated

Cannabidivarin
Cannabidivarin.svg
Cannabidivarin molecule ball.png
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.236.933 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H26O2
Molar mass 286.415 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 Yes check.svgY
  • Key:REOZWEGFPHTFEI-CVEARBPZSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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).

Contents

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

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.
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