Record Information
Version1.0
Creation date2015-05-07 21:33:13 UTC
Update date2018-05-28 18:38:48 UTC
Primary IDFDB031310
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameΔ9tetrahydrocannabinol
DescriptionΔ9tetrahydrocannabinol, also known as delta(9)-thc or marinol, is a member of the class of compounds known as 2,2-dimethyl-1-benzopyrans. 2,2-dimethyl-1-benzopyrans are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Δ9tetrahydrocannabinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Δ9tetrahydrocannabinol can be found in a number of food items such as wakame, cloves, burbot, and black cabbage, which makes Δ9tetrahydrocannabinol a potential biomarker for the consumption of these food products. Δ9tetrahydrocannabinol can be found primarily in blood and urine. Δ9tetrahydrocannabinol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Δ9tetrahydrocannabinol is a drug which is used for the treatment of anorexia associated with weight loss in patients with aids, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatment. The mechanism of action of marinol is not completely understood. It is thought that cannabinoid receptors in neural tissues may mediate the effects of dronabinol and other cannabinoids. Animal studies with other cannabinoids suggest that marinol's antiemetic effects may be due to inhibition of the vomiting control mechanism in the medulla oblongata (DrugBank). A potentially serious oral ingestion, if recent, should be managed with gut decontamination. In unconscious patients with a secure airway, instill activated charcoal (30 to 100 g in adults, 1 to 2 g/kg in infants) via a nasogastric tube. A saline cathartic or sorbitol may be added to the first dose of activated charcoal. Patients experiencing depressive, hallucinatory or psychotic reactions should be placed in a quiet area and offered reassurance. Benzodiazepines (5 to 10 mg diazepam po) may be used for treatment of extreme agitation. Hypotension usually responds to Trendelenburg position and IV fluids. Pressors are rarely required (L1712) (T3DB).
CAS Number1972-08-3
Structure
Thumb
Synonyms
SynonymSource
(-)-delta9-trans-TetrahydrocannabinolChEBI
1-trans-delta-9-TetrahydrocannabinolChEBI
3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-olChEBI
6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olChEBI
Delta(1)-TetrahydrocannabinolChEBI
delta9-TetrahydrocannabinolChEBI
Delta(9)-THCChEBI
DronabinolChEBI
DronabinolumChEBI
SyndrosChEBI
MarinolKegg
THCKegg
(-)-Δ9-trans-tetrahydrocannabinolGenerator
1-trans-Δ-9-tetrahydrocannabinolGenerator
Δ(1)-tetrahydrocannabinolGenerator
Δ9-tetrahydrocannabinolGenerator
Δ(9)-THCGenerator
DELTA-9-THCHMDB
DELTA-9-TETRAHYDROCANNABINOLHMDB
Δ-9-THCHMDB
Δ-9-tetrahydrocannabinolHMDB
Tetrahydrocannabinol, (6a-trans)-isomerHMDB
9-Ene-tetrahydrocannabinolHMDB
Tetrahydrocannabinol, (6ar-cis)-isomerHMDB
Tetrahydrocannabinol, (6as-cis)-isomerHMDB
Tetrahydrocannabinol, trans isomerHMDB
delta(9)-TetrahydrocannabinolHMDB
delta(1)-THCHMDB
9 Ene tetrahydrocannabinolHMDB
Solvay brand OF tetrahydrocannabinolHMDB
Tetrahydrocannabinol, trans-(+-)-isomerHMDB
Tetrahydrocannabinol, trans-isomerHMDB
delta 1-TetrahydrocannabinolHMDB
(-)- delta 9-TetrahydrocannabinolHMDB
(-)-delta 1-TetrahydrocannabinolHMDB
(-)-delta 9-THCHMDB
(-)-delta 9-trans-TetrahydrocannabinolHMDB
(-)-trans-delta 1-TetrahydrocannabinolHMDB
(-)-trans-delta 9-TetrahydrocannabinolHMDB
(-)-trans-delta 9-THCHMDB
(L)-delta 1-TetrahydrocannabinolHMDB
1-trans-delta 9-TetrahydrocannabinolHMDB
14C-delta 1-TetrahydrocannabinolHMDB
delta 1-THCHMDB
delta 9-TetrahydrocannabinolHMDB
delta 9-THCHMDB
delta 9-trans-TetrahydrocannabinolHMDB
Exocyclic delta (9)(11)-tetrahydrocannabiolHMDB
L-delta 1-trans-TetrahydrocannabinolHMDB
L-trans-delta 9-TetrahydrocannabinolHMDB
PrimolutHMDB
trans-delta (-)-9-TetrahydrocannabinolHMDB
trans-delta 9-TetrahydrocannabinolHMDB
TetrahydrocannabinolChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP7.29ALOGPS
logP5.94ChemAxon
logS-5.1ALOGPS
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 Count4ChemAxon
Refractivity96.73 m³·mol⁻¹ChemAxon
Polarizability38.96 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30O2
IUPAC name(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
InChI IdentifierInChI=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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChI KeyCYQFCXCEBYINGO-IAGOWNOFSA-N
Isomeric SMILES[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21
Average Molecular Weight314.4617
Monoisotopic Molecular Weight314.224580204
Classification
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 Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0597-4090000000-670e40c1592b93325e44View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-6009000000-735bce5abc1be2637810View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1239000000-dd0a437774bcd5f12cd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-6291000000-48cdeee605af2033e358View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9140000000-f6fc10c62a978b5bb9b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-1a8c2415357935328858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0429000000-d0c2b14e825c4f547980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01re-3930000000-3f6ef979ec17030832a8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01pp-4792000000-06532e533cb7794b7c37View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference