Showing Compound Card for Delta-8-tetrahydrocannabinol (CDB000024)

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Record Information
Version1.0
Created at2020-03-19 00:36:02 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000024
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-8-tetrahydrocannabinol
DescriptionDelta-8-tetrahydrocannabinol, also known as delta-8-THC, 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. Delta-8-THC and its acid precursor are considered as THC and THC acid artifacts, respectively. The 8,9 double-bond position is thermodynamically more stable than the 9,10 position. Delta-8-THC is a neutral compound and it is one of more than 120 cannabinoid compounds that are known in cannabis plant. Delta-8-tetrahydrocannabinol is a minor constituent of most varieties of marijuana in which its double-bond isomer, delta-9-THC, predominates. (PMID: 6991645 ). It is a partial agonist for cannabinoid type one (CB1) / type 2 (CB2) receptors and the activation of CB1/CB2 inhibits adenylyl cyclase, activates potassium channels, or reduces calcium channel conductance (PMID: 20166921 ; DOI: 10.1016/bs.ant.2018.10.006). It has also been shown to be pharmacologically active as an antiglaucoma agent (PMID: 12182967 ; PMID: 1328979 ). Delta-8-THC is easier and less expensive to prepare and is less psychotropic than delta-9-THC (PMID: 1328979 ; PMID: 15099912 ; PMID: 15025853 ; PMID: 15067692 ). Additionally, delta-8-THC is chemically more stable, does not undergo oxidation to cannabinol and has a much longer shelf life than delta-9-THC (PMID: 1328979 ). Moreover, it has been shown to exhibit negligible side effects when administered prior to antineoplastic therapy in cancer patients (PMID: 15067692 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H30O2
Average Molecular Weight314.47
Monoisotopic Molecular Weight314.2246
IUPAC Name(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol
Traditional Name(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6aH,7H,10H,10aH-benzo[c]isochromen-1-ol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2[C@H]3CC(C)=CC[C@H]3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9,12-13,16-17,22H,5-8,10-11H2,1-4H3/t16-,17+/m0/s1
InChI KeyHCAWPGARWVBULJ-DLBZAZTESA-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
  • Phenol
  • 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
logP7.65ALOGPS
logP5.94ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)10.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.73 m³·mol⁻¹ChemAxon
Polarizability38.53 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelta-8-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View 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
Not Available
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 Compound86308458
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. Reggio PH: Endocannabinoid binding to the cannabinoid receptors: what is known and what remains unknown. Curr Med Chem. 2010;17(14):1468-86. doi: 10.2174/092986710790980005. [PubMed:20166921 ]
  3. Jarvinen T, Pate DW, Laine K: Cannabinoids in the treatment of glaucoma. Pharmacol Ther. 2002 Aug;95(2):203-20. doi: 10.1016/s0163-7258(02)00259-0. [PubMed:12182967 ]
  4. Muchtar S, Almog S, Torracca MT, Saettone MF, Benita S: A submicron emulsion as ocular vehicle for delta-8-tetrahydrocannabinol: effect on intraocular pressure in rabbits. Ophthalmic Res. 1992;24(3):142-9. doi: 10.1159/000267160. [PubMed:1328979 ]
  5. Avraham Y, Ben-Shushan D, Breuer A, Zolotarev O, Okon A, Fink N, Katz V, Berry EM: Very low doses of delta 8-THC increase food consumption and alter neurotransmitter levels following weight loss. Pharmacol Biochem Behav. 2004 Apr;77(4):675-84. doi: 10.1016/j.pbb.2004.01.015. [PubMed:15099912 ]
  6. Stinchcomb AL, Valiveti S, Hammell DC, Ramsey DR: Human skin permeation of Delta8-tetrahydrocannabinol, cannabidiol and cannabinol. J Pharm Pharmacol. 2004 Mar;56(3):291-7. doi: 10.1211/0022357022791. [PubMed:15025853 ]
  7. Valiveti S, Hammell DC, Earles DC, Stinchcomb AL: In vitro/in vivo correlation studies for transdermal delta 8-THC development. J Pharm Sci. 2004 May;93(5):1154-64. doi: 10.1002/jps.20036. [PubMed:15067692 ]