Showing Compound Card for Tetrahydrocannabivarin (CDB006400)

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Record Information
Version1.0
Created at2021-01-13 17:44:35 UTC
Updated at2021-01-13 17:44:36 UTC
CannabisDB IDCDB006400
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTetrahydrocannabivarin
DescriptionTetrahydrocannabivarin 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Plants with elevated levels of propyl cannabinoids (including THCV) have been found in populations of Cannabis sativa L. ssp. indica ( Cannabis indica Lam.) from China, India, Nepal, Thailand, Afghanistan, and Pakistan, as well as southern and western Africa. THCV levels up to 53.7% of total cannabinoids have been reported (PMID: 4752132 ). THCV is a cannabinoid receptor type 1 antagonist and cannabinoid receptor type 2 partial agonist. Delta8-THCV has also been shown to be a CB1 antagonist. THCV is a new potential treatment against obesity-associated glucose intolerance with pharmacology different from that of CB1 inverse agonists/antagonists. GW Pharmaceuticals is studying plant-derived tetrahydrocannabivarin (as GWP42004) for type 2 diabetes in addition to metformin. 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. Similar to THC, THCV has 7 double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism). THCV could be considered an analog of THC, in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act. Tetrahydrocannabivarin is also a constituent of cannabis smoke. Tetrahydrocannabivarin is volatilized during the combustion of cannabis.
Structure
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MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC20H28O
Average Molecular Weight284.443
Monoisotopic Molecular Weight284.214015522
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
[H][C@]12C=C(C)CC[C@]1([H])C(C)(C)CC1=C2C(O)=CC(CCC)=C1
InChI Identifier
InChI=1S/C20H28O/c1-5-6-14-10-15-12-20(3,4)17-8-7-13(2)9-16(17)19(15)18(21)11-14/h9-11,16-17,21H,5-8,12H2,1-4H3/t16-,17-/m0/s1
InChI KeyYAIZLDHAZZCEJJ-IRXDYDNUSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
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Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
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Pathways
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Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
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HMDB IDNot Available
DrugBank IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Hadley K, Fetterman PS: Constituents of Cannabis sativa L. VI. Propyl homologs in samples of known geographical origin. J Pharm Sci. 1973 Oct;62(10):1739-41. doi: 10.1002/jps.2600621045. [PubMed:4752132 ]