Cannabidivarin

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 ;
DrugBank	none ;
ChemSpider	21106275 ;
ECHA InfoCard	100.236.933
Chemical and physical data
Formula	C19H26O2
Molar mass	286.41 g/mol
3D model (Jmol)	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 ; Key:REOZWEGFPHTFEI-CVEARBPZSA-N ;
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Cannabidivarin (CBDV) is a non-psychoactive cannabinoid found in Cannabis. It is a homolog of cannabidiol (CBD), with the side-chain shortened by two methylene bridges (CH₂ units). Plants with relatively high 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] CBDV has anticonvulsant effects.^[3]

Similarly to CBD, it has 7 double bond isomers and 30 stereoisomers (see: Cannabidiol#Double bond isomers and their stereoisomers). It is not scheduled by Convention on Psychotropic Substances. It is being actively developed by GW Pharmaceuticals^[4] (as GWP42006) because of a demonstrated neurochemical pathway for previously-observed anti-epileptic and anti-convulsive action.^[5] GW has begun a phase 2 trial for adult epilepsy,^[6] and is to begin trials of this CBDV product in children in 2016 in Australia.^[7]^[8]

References[edit]

^ 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.
^ 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.
^ 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.
^ http://www.gwpharm.com/therapeutic-areas.aspx^{[full citation needed]}
^ 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.
^ "GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy" (Press release). GW Pharmaceuticals. May 6, 2015. Retrieved November 10, 2015.
^ "GW Pharma Press release".
^ "NSW advice to practitioners on Medical Cannabis trials" (PDF).

External links[edit]

Erowid Compounds found in Cannabis sativa

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

[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.

[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] 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.

[4] ttp://www.gwpharm.com/therapeutic-areas.aspx^{[full citation needed]}

[5] 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.

[6] "GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy" (Press release). GW Pharmaceuticals. May 6, 2015. Retrieved November 10, 2015.

[7] "GW Pharma Press release".

[8] "NSW advice to practitioners on Medical Cannabis trials" (PDF).

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Cannabidivarin

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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
DrugBank	none^N
ChemSpider	21106275^Y
ECHA InfoCard	100.236.933
Chemical and physical data
Formula	C₁₉H₂₆O₂
Molar mass	286.41 g/mol
3D model (Jmol)	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)