Cannabidivarin (CBDV , GWP42006 ) 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).
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#Double bond isomers and their stereoisomers ). 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 [ ]
List of investigational analgesics
References [ ]
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ "GW Pharmaceuticals Announces Preliminary Results of Phase 2a Study for its Pipeline Compound GWP42006" . GW Pharmaceuticals. 21 February 2018. Retrieved 28 May 2019 .
^ 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" . Archived from the original on 2015-11-21.
^ "NSW advice to practitioners on Medical Cannabis trials" (PDF) . Archived from the original (PDF) on 2015-11-21.
External links [ ]
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles
AM-630
AM-679
AM-694
AM-1241
AM-2233
GW-405,833 (L-768,242)
Pravadoline
RCS-4
WIN 54,461
Cyclohexylphenols Eicosanoids
ACEA
ACPA
Methanandamide (AM-356)
O-1812
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
AM-251
AM-630
AM-6545
BML-190
Drinabant (AVE1625)
Hemopressin
Ibipinabant (SLV319)
JTE-907
LY-320,135
MK-9470
NESS-0327
O-1918
O-2050
Otenabant (CP-945,598)
PF-514273
PipISB
PSB-SB-487
Rimonabant (SR141716)
Rosonabant (E-6776)
SR-144,528
Surinabant (SR147778)
Taranabant (MK-0364)
TM-38837
VCHSR
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (ginger , Sichuan and melegueta peppers )
Acrolein
Allicin (garlic )
Allyl isothiocyanate (mustard , radish , horseradish , wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis )
Cannabidiol (cannabis )
Cannabigerol (cannabis )
Cinnamaldehyde (cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin )
Curcumin (turmeric )
(celery )
Diallyl disulfide
Dicentrine (Lindera spp.)
Formalin
Gingerols (ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
(celery , Angelica acutiloba )
Linalool (Sichuan pepper , thyme )
Methylglyoxal
Methyl salicylate (wintergreen )
N-Methylmaleimide
Nicotine (tobacco )
Oleocanthal (olive oil )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper )
Shogaols (ginger , Sichuan and melegueta peppers )
Tear gases
Tetrahydrocannabinol (cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
Activators
Adhyperforin (St John's wort )
Diacyl glycerol
GSK1702934A
Hyperforin (St John's wort )
Substance P
Blockers
DHEA-S
Flufenamic acid
GSK417651A
Meclofenamic acid
N-(p-Amylcinnamoyl)anthranilic acid
Niflumic acid
Pregnenolone sulfate
Progesterone
Tolfenamic acid
TRPM
Activators
ADP-ribose
Calcium (intracellular)
CIM-0216
Cold
Cooling Agent 10
Eucalyptol (eucalyptus )
Geraniol
Hydroxycitronellal
Icilin
Linalool
Menthol (mint )
Pregnenolone sulfate
(Ruta graveolens )
Steviol glycosides (e.g., stevioside ) (Stevia rebaudiana )
Sweet tastants (e.g., glucose , fructose , sucrose ; indirectly)
WS-12
Blockers
AMG-333
Capsazepine
Clotrimazole
Flufenamic acid
Meclofenamic acid
Mefenamic acid
N-(p-Amylcinnamoyl)anthranilic acid
Nicotine (tobacco )
Niflumic acid
Ononetin
PF-05105679
RQ-00203078
Ruthenium red
(Ruta graveolens )
Tolfenamic acid
TPPO
TRPM4-IN-5
TRPML
TRPP
Activators
Triptolide (Tripterygium wilfordii )
Blockers
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (ginger , Sichuan and melegueta peppers )
Allicin (garlic )
AM404
Anandamide
(Andrographis paniculata )
Camphor (camphor laurel , rosemary , camphorweed , African blue basil , camphor basil )
Cannabidiol (cannabis )
Cannabidivarin (cannabis )
Capsaicin (chili pepper )
Carvacrol (oregano , thyme , pepperwort , wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (chili pepper )
Estradiol
Eugenol (basil , clove )
Evodiamine (Euodia ruticarpa )
Gingerols (ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (chili pepper )
Homodihydrocapsaicin (chili pepper )
Incensole (incense )
Lysophosphatidic acid
Low pH (acidic conditions)
Menthol (mint )
N-Arachidonoyl dopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (PAVA spray )
Nordihydrocapsaicin (chili pepper )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g., )
Piperine (black pepper , long pepper )
Polygodial (Dorrigo pepper )
Probenecid
Protons
RhTx
(Ruta graveolens )
Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii )
Shogaols (ginger , Sichuan and melegueta peppers )
Tetrahydrocannabivarin (cannabis )
Thymol (thyme , oregano )
Tinyatoxin (Euphorbia resinifera /pooissonii )
Tramadol
Vanillin (vanilla )
Zucapsaicin
Blockers
α-Spinasterol (Vernonia tweediana )
AMG-517
AMG-9810
Cannabigerol (cannabis )
Cannabigerolic acid (cannabis )
Cannabigerovarin (cannabis )
Cannabinol (cannabis )
Capsazepine
DHEA
DHEA-S
Flufenamic acid
GRC-6211
HC-067047
Lanthanum
Mavatrep
Meclofenamic acid
N-(p-Amylcinnamoyl)anthranilic acid
Niflumic acid
Pregnenolone sulfate
RN-9893
Ruthenium red
SB-366791
SB-705498
Tolfenamic acid
TRPV3-74a
See also: Receptor/signaling modulators • Ion channel modulators