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Δ9tetrahydrocannabinol (FDB031310)

Record Information
Version1.0
Creation date2015-05-07 21:33:13 UTC
Update date2020-09-17 15:29:19 UTC
Primary IDFDB031310
Secondary Accession Numbers
  • FDB001065
Chemical Information
FooDB NameΔ9tetrahydrocannabinol
DescriptionDelta-9-Tetrahydrocannabinol, also known as tetrahydrocannabinol or 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. THC is also chemically or biochemically classified as a diterpenoid. Formally it can be described as a 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. Tetrahydrocannabinol (THC) is one of at least 113 cannabinoids identified in cannabis (PMID: 26836472). In the cannabis plant THC (like most plant terpenes) is used in self-defense, mostly to protect itself against insect predation, ultraviolet light, and other environmental stressors. THC is the principal psychoactive constituent of cannabis, responsible for the “high” that users experience (https://doi.org/10.1021/ja01062a046). The psychoactivity of THC results from its partial agonist activity of the cannabinoid receptor CB1 (Ki = 10 nM), located mainly in the central nervous system, and the CB2 receptor (Ki = 24 nM), mainly found in cells of the immune system. THC activation of these cannabinoid receptors, especially the CB1 receptor, leads to a decrease in the concentration of the second messenger molecule cAMP in synaptosomes and brain synapses through inhibition of adenylate cyclase (PMID: 9260875; PMID: 1848340). In cannabis plants, THC occurs mainly as tetrahydrocannabinolic acid (THCA). THCA is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme Geranyl-pyrophosphate—olivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THCA. Over time, or when heated (via vaping or smoking), THCA is decarboxylated, producing THC. THC (either as a pure drug or through ingestion/inhalation via medical marijuana) is used for the treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments. THC has been formulated into several commercially available oral drugs. Dronabinol is the generic name for the oral form of synthetic THC and is marketed in the U.S. as Marinol. It is indicated for the treatment of severe CINV (chemotherapy-induced nausea and vomiting) in cancer patients, and for AIDS-related anorexia associated with weight loss. Nabilone is the generic name for an orally administered synthetic structural analogue of THC, which is marketed in Canada as Cesamet but also now available in generic forms (e.g. RAN-nabilone, PMS-nabilone, TEVA-nabilone, CO- nabilone, ACT-nabilone). It is indicated for severe CINV in cancer patients. THC is an active ingredient in another drug called Nabiximols, a specific extract of Cannabis that was approved as a botanical drug in the United Kingdom in 2010 as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain, spasticity, overactive bladder, and other symptoms.
CAS Number1972-08-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Physiological effect

Health effect:

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Route of exposure:

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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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01pp-4792000000-06532e533cb7794b7c372014-09-20View Spectrum
Predicted GC-MSMaxepa, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0597-4090000000-670e40c1592b93325e44Spectrum
Predicted GC-MSMaxepa, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-6009000000-735bce5abc1be2637810Spectrum
Predicted GC-MSMaxepa, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMaxepa, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-0219000000-1916f155ea706f1bfd782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-05mx-3943000000-9b0e61162051930e030f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-052f-3920000000-06615e927292d6b78f042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-006x-5900000000-c44a1196b35ae31ac75c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-00xu-7900000000-d06351b5900dfe483bd62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-00tf-9600000000-14d6a1649ef828de05e32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-00mo-9400000000-c1c5f46aa3925b6b440f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-00ou-9300000000-fec356cc420b4d525c372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-016u-9200000000-295f54d67e0fa95127782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 71V, positivesplash10-0fvl-9200000000-92620f75edee112202672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-053f-0980000000-c5e3986b120b13bf6cad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00dr-0900000000-71e91d90ab20dda218792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0002-9000000000-0c6530b23f4594b0199d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-03di-0910000000-13e75d88a02fafe0bbe22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-000j-0900000000-ae7ab2b9c0db456ba4d42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00lr-0490000000-aebf4a983943679cba932020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-0910000000-13eb5c07bf46dbbbc6c32020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1239000000-dd0a437774bcd5f12cd92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-6291000000-48cdeee605af2033e3582016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9140000000-f6fc10c62a978b5bb9b02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-1a8c24153579353288582016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0429000000-d0c2b14e825c4f5479802016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01re-3930000000-3f6ef979ec17030832a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-2514638890974c4f71f32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-f9f1dddf06624032e0de2021-09-23View Spectrum
NMR
TypeDescriptionView
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
Food Biomarker OntologyNot Available
VMH 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