Showing Compound Card for Delta-9-tetrhydrocannabivarin (CDB000021)

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Record Information
Version1.0
Created at2020-03-19 00:35:48 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000021
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-9-tetrhydrocannabivarin
DescriptionDelta-9-Tetrahydrocannabivarin belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Tetrahydrocannabivarin is a neutral compound. Delta-9-Tetrahydrocannabivarin (THCV, THV) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of a pentyl (5-carbon) group on the molecule, which makes it produce very different effects from THC. Delta-9-Tetrahydrocannabivarin is one of the Delta-9-THC type cannabinoid compounds that are known in cannabis plant. Some cannabis compounds are used as medicine. Delta-9-Tetrahydrocannabivarin's main pharmacological characteristics are as an analgesic and an euphoriant. (PMID: 6991645 ). It is a cannabis receptor type-1(CB1) and cannabis receptor type-2(CB2) antagonist (PMID: 16205722 ) and a CB2 agonist at higher doses, which attenuate inflammation and hyperalgesia in mice (PMID: 20590571 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC19H26O2
Average Molecular Weight286.42
Monoisotopic Molecular Weight286.1933
IUPAC Name(6aR,10aR)-6,6,9-trimethyl-3-propyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional Nametetrahydrocannabivarin
CAS Registry Number31262-37-0
SMILES
CCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1
InChI KeyZROLHBHDLIHEMS-HUUCEWRRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.08ALOGPS
logP5.06ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.53 m³·mol⁻¹ChemAxon
Polarizability34.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelta-9-tetrhydrocannabivarin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-000i-0190000000-331d6705c304885b14402020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-00kr-0490000000-40ea350ed7e89e4801a62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-02t9-0980000000-453b3fa43abfb644d3a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-02t9-0940000000-edb25ce25e596c0962732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, negativesplash10-0cfr-0920000000-7ddb17adece71d76bf032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-056r-1910000000-eba782e6aedc291c39c72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 35V, negativesplash10-056r-1910000000-7d9c90746788a9e6133b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-05ea-2900000000-903a2853f97ed2e726922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-05x1-3900000000-a2a93b0a118db0f11de72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, negativesplash10-014i-0690000000-149e4cc21e3357cebf322020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, negativesplash10-0a4i-0900000000-ae3004bb674d9632cd0c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, negativesplash10-1001-0950000000-28411c9e589f4780eb862020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, negativesplash10-004i-9000000000-0ae8d2338f48c17984cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, negativesplash10-00di-0900000000-f7532366ffd4f4743bee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-000i-0390000000-840599892ce5ccfe34c92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-000i-1690000000-68aafb161f96d264e6522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00kr-2970000000-22c296b4bc109801a8ad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-0670-2940000000-aca79f1348c5029079f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-014i-2930000000-3e9edadf0dedb85246412020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1190000000-701fa72e47e851b57ea12017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-5390000000-f306def86044beeb03472017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9330000000-574e68eaa9c8ee1010f12017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-e8ab8ecdb8fc182a4e472017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0490000000-8a4e6ac5ddc6b4b017e12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsd-3940000000-6df72ba145590b430e952017-07-26View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Cannabinoid receptor 1CNR16q14-q15P21554 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified1.300 mg/g dry wt details
97 SageDetected and Quantified1.740 mg/g dry wt details
AdonisDetected and Quantified11.100 mg/g dry wt details
Alien BluesDetected and Quantified0.9 +/- 0.6 mg/g dry wt details
Alien DawgDetected and Quantified0.337 mg/g dry wt
    • David S. Wishart,...
 details
Alien Sour AppleDetected and Quantified1.500 mg/g dry wt details
Black BossDetected and Quantified1.780 mg/g dry wt details
Blue Cherry PieDetected and Quantified1 +/- 0.6 mg/g dry wt details
Blue DreamDetected and Quantified0.3 +/- 0.1 mg/g dry wt details
Blue DreamDetected and Quantified0.697 mg/g dry wt details
Blue DreamDetected and Quantified0.710 mg/g dry wt details
Blue DreamDetected and Quantified1.860 mg/g dry wt details
Blue DreamDetected and Quantified1.920 mg/g dry wt details
Bob MarleyDetected and Quantified0.930 mg/g dry wt details
Bohdi TreeDetected and Quantified0.2 +/- 0 mg/g dry wt details
ChemdawgDetected and Quantified1.780 mg/g dry wt details
Chemdawg #4Detected and Quantified1.530 mg/g dry wt details
Chemdawg #4Detected and Quantified1.760 mg/g dry wt details
Cold Creek KushDetected and Quantified0.6 +/- 0 mg/g dry wt details
Cookies and CreamDetected and Quantified1.080 mg/g dry wt details
Cosmic LotusDetected and Quantified0.706 mg/g dry wt details
Crystal CookiesDetected and Quantified9.7 +/- 1.2 mg/g dry wt details
Dairy QueenDetected and Quantified0.675 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.621 mg/g dry wt details
Double Royal KushDetected and Quantified0.8 +/- 0.2 mg/g dry wt details
FLODetected and Quantified0.7 +/- 0.2 mg/g dry wt details
FLODetected and Quantified0.872 mg/g dry wt details
GabriolaDetected and Quantified0.258 mg/g dry wt
    • David S. Wishart,...
 details
Goji OGDetected and Quantified0.948 mg/g dry wt details
Golden CobraDetected and Quantified0.458 mg/g dry wt details
Golden SageDetected and Quantified2.270 mg/g dry wt details
Gorilla GlueDetected and Quantified1.180 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.812 mg/g dry wt details
Grandaddy PurpleDetected and Quantified0.5 +/- 0 mg/g dry wt details
Grape StomperDetected and Quantified0.473 mg/g dry wt details
Grape StomperDetected and Quantified0.484 mg/g dry wt details
Green CrackDetected and Quantified1.6 +/- 0.1 mg/g dry wt details
Green Crack 2015Detected and Quantified1.2 +/- 0.1 mg/g dry wt details
Grizzly KushDetected and Quantified5.990 mg/g dry wt details
Hash PlantDetected and Quantified0.446 mg/g dry wt details
Hash PlantDetected and Quantified0.788 mg/g dry wt details
HemlockDetected and Quantified1.340 mg/g dry wt details
Holy PowerDetected and Quantified1.6 +/- 0.1 mg/g dry wt details
Island HoneyDetected and Quantified0.159 mg/g dry wt
    • David S. Wishart,...
 details
JabberwockyDetected and Quantified1.680 mg/g dry wt details
JabberwockyDetected and Quantified1.830 mg/g dry wt details
JuanitaDetected and Quantified0.2 +/- 0 mg/g dry wt details
Kandy KushDetected and Quantified0.413 mg/g dry wt details
Kush PuppyDetected and Quantified0.402 mg/g dry wt details
La ChocoDetected and Quantified0.884 mg/g dry wt details
LavendarDetected and Quantified0.5 +/- 0.1 mg/g dry wt details
LavendarDetected and Quantified0.9 +/- 0 mg/g dry wt details
Lavendar Jones 2015Detected and Quantified1 +/- 0.1 mg/g dry wt details
Lemon BalmDetected and Quantified0.557 mg/g dry wt details
Lemon GojiDetected and Quantified0.187 mg/g dry wt details
Lemon OGDetected and Quantified1.040 mg/g dry wt details
Lemon SherbetDetected and Quantified1.280 mg/g dry wt details
Lemon SkunkDetected and Quantified0.577 mg/g dry wt details
Lemon SkunkDetected and Quantified0.693 mg/g dry wt details
Liberty HazeDetected and Quantified0.926 mg/g dry wt details
LohanDetected and Quantified0.916 mg/g dry wt details
Love LaceDetected and Quantified3.9 +/- 0.3 mg/g dry wt details
Maui HazeDetected and Quantified0.968 mg/g dry wt details
Moby DickDetected and Quantified1.200 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified0.174 mg/g dry wt details
Nightmare CookieDetected and Quantified0.134 mg/g dry wt details
OracleDetected and Quantified0.8 +/- 0.1 mg/g dry wt details
Orange SkunkDetected and Quantified0.132 mg/g dry wt details
Pipe DreamDetected and Quantified0.769 mg/g dry wt details
Platinum BuffaloDetected and Quantified13 +/- 0.5 mg/g dry wt details
Platinum DelightDetected and Quantified0.166 mg/g dry wt details
Platinum GorillaDetected and Quantified4 +/- 0.2 mg/g dry wt details
Platinum ScoutDetected and Quantified10.1 +/- 0.3 mg/g dry wt details
Purple EclipseDetected and Quantified1.140 mg/g dry wt details
Purple Fat PieDetected and Quantified0.5 +/- 0.1 mg/g dry wt details
QuadraDetected and Quantified0.287 mg/g dry wt
    • David S. Wishart,...
 details
RomulinDetected and Quantified1.3 +/- 0.3 mg/g dry wt details
Rosetta StoneDetected and Quantified0.494 mg/g dry wt details
RXDetected and Quantified2.2 +/- 0.2 mg/g dry wt details
Sensi StarDetected and Quantified0.448 mg/g dry wt
    • David S. Wishart,...
 details
SkywalkerDetected and Quantified0.7 +/- 0 mg/g dry wt details
Skywalker OGDetected and Quantified2.010 mg/g dry wt details
Sour WillieDetected and Quantified0.2 +/- 0 mg/g dry wt details
SpectrumDetected and Quantified0.144 mg/g dry wt details
Strawberry FieldsDetected and Quantified2.290 mg/g dry wt details
Strawberry FieldsDetected and Quantified2.510 mg/g dry wt details
Sunset SherbetDetected and Quantified0.611 mg/g dry wt details
Sunset SherbetDetected and Quantified0.688 mg/g dry wt details
Tangerine DreamDetected and Quantified0.258 mg/g dry wt
    • David S. Wishart,...
 details
ThunderstruckDetected and Quantified0.5 +/- 0.1 mg/g dry wt details
Twisted VelvetDetected and Quantified1.3 +/- 0.2 mg/g dry wt details
Venom OGDetected and Quantified1.070 mg/g dry wt details
Walker KushDetected and Quantified0.8 +/- 0.1 mg/g dry wt details
White WidowDetected and Quantified0.5 +/- 0.1 mg/g dry wt details
White WidowDetected and Quantified0.822 mg/g dry wt details
Wonder WomanDetected and Quantified0.986 mg/g dry wt details
HMDB IDNot Available
DrugBank IDDB11755
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrocannabivarin
METLIN IDNot Available
PubChem Compound93147
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Thomas A, Stevenson LA, Wease KN, Price MR, Baillie G, Ross RA, Pertwee RG: Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist. Br J Pharmacol. 2005 Dec;146(7):917-26. doi: 10.1038/sj.bjp.0706414. [PubMed:16205722 ]
  3. Bolognini D, Costa B, Maione S, Comelli F, Marini P, Di Marzo V, Parolaro D, Ross RA, Gauson LA, Cascio MG, Pertwee RG: The plant cannabinoid Delta9-tetrahydrocannabivarin can decrease signs of inflammation and inflammatory pain in mice. Br J Pharmacol. 2010 Jun;160(3):677-87. doi: 10.1111/j.1476-5381.2010.00756.x. [PubMed:20590571 ]