Record Information
Version1.0
Created at2020-03-19 00:35:40 UTC
Updated at2020-12-07 19:07:25 UTC
CannabisDB IDCDB000001
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-9-tetrahydrocannabinol
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 ( Ref:DOI ). 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.
Structure
Thumb
Synonyms
ValueSource
(-)-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
THCKegg
MarinolKegg
(-)-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
(-)-3,4-trans-delta1-TetrahydrocannabinolPhytoBank
(-)-3,4-trans-Δ1-TetrahydrocannabinolPhytoBank
(-)-delta1-TetrahydrocannabinolPhytoBank
(-)-delta9-THCPhytoBank
(-)-delta9-TetrahydrocannabinolPhytoBank
(-)-trans-delta1-TetrahydrocannabinolPhytoBank
(-)-trans-delta9-THCPhytoBank
(-)-trans-delta9-TetrahydrocannabinolPhytoBank
(-)-trans-Δ1-TetrahydrocannabinolPhytoBank
(-)-trans-Δ9-THCPhytoBank
(-)-trans-Δ9-TetrahydrocannabinolPhytoBank
(-)-Δ1-TetrahydrocannabinolPhytoBank
(-)-Δ9-THCPhytoBank
(-)-Δ9-TetrahydrocannabinolPhytoBank
(l)-delta1-TetrahydrocannabinolPhytoBank
(l)-Δ1-TetrahydrocannabinolPhytoBank
delta1-THCPhytoBank
delta1-TetrahydrocannabinolPhytoBank
delta9-THCPhytoBank
delta9-trans-TetrahydrocannabinolPhytoBank
l-delta1-trans-TetrahydrocannabinolPhytoBank
l-trans-delta9-TetrahydrocannabinolPhytoBank
l-trans-Δ9-TetrahydrocannabinolPhytoBank
l-Δ1-trans-TetrahydrocannabinolPhytoBank
trans-(-)-delta9-TetrahydrocannabinolPhytoBank
trans-(-)-Δ9-TetrahydrocannabinolPhytoBank
trans-delta9-TetrahydrocannabinolPhytoBank
trans-Δ9-TetrahydrocannabinolPhytoBank
Δ1-THCPhytoBank
Δ1-TetrahydrocannabinolPhytoBank
Δ9-THCPhytoBank
Δ9-trans-TetrahydrocannabinolPhytoBank
Chemical FormulaC21H30O2
Average Molecular Weight314.46
Monoisotopic Molecular Weight314.2246
IUPAC Name(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional NameTHC
CAS Registry Number1972-08-3
SMILES
CCCCCC1=CC(O)=C2[C@@H]3C=C(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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChI KeyCYQFCXCEBYINGO-IAGOWNOFSA-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 Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0026 g/LNot Available
logP5.648Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01pp-4792000000-06532e533cb7794b7c37Spectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0597-4090000000-670e40c1592b93325e44Spectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-6009000000-735bce5abc1be2637810Spectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-0219000000-1916f155ea706f1bfd78Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-05mx-3943000000-9b0e61162051930e030fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-052f-3920000000-06615e927292d6b78f04Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-006x-5900000000-c44a1196b35ae31ac75cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-00xu-7900000000-d06351b5900dfe483bd6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-00tf-9600000000-14d6a1649ef828de05e3Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-00mo-9400000000-c1c5f46aa3925b6b440fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-00ou-9300000000-fec356cc420b4d525c37Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-016u-9200000000-295f54d67e0fa9512778Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 71V, positivesplash10-0fvl-9200000000-92620f75edee11220267Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-053f-0980000000-c5e3986b120b13bf6cadSpectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00dr-0900000000-71e91d90ab20dda21879Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0002-9000000000-0c6530b23f4594b0199dSpectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-03di-0910000000-13e75d88a02fafe0bbe2Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-000j-0900000000-ae7ab2b9c0db456ba4d4Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00lr-0490000000-aebf4a983943679cba93Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-0910000000-13eb5c07bf46dbbbc6c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1239000000-dd0a437774bcd5f12cd9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-6291000000-48cdeee605af2033e358Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9140000000-f6fc10c62a978b5bb9b0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-1a8c2415357935328858Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0429000000-d0c2b14e825c4f547980Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01re-3930000000-3f6ef979ec17030832a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-2514638890974c4f71f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-f9f1dddf06624032e0deSpectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Multidrug resistance protein 1ABCB17q21.12P08183 details
ATP-binding cassette sub-family G member 2ABCG24q22Q9UNQ0 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
Cytochrome P450 1A1CYP1A115q24.1P04798 details
Cytochrome P450 2A6CYP2A619q13.2P11509 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Cannabinoid receptor 1CNR16q14-q15P21554 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien BluesDetected and Quantified86.6 +/- 11.6 mg/g dry wt details
Alien DawgDetected and Quantified1.03 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Blue Cherry PieDetected and Quantified98 +/- 22.5 mg/g dry wt details
Blue DreamDetected and Quantified109.9 +/- 24.1 mg/g dry wt details
Bohdi TreeDetected and Quantified38.3 +/- 15.5 mg/g dry wt details
Cold Creek KushDetected and Quantified88.8 +/- 42.8 mg/g dry wt details
Crystal CookiesDetected and Quantified170.7 +/- 18.5 mg/g dry wt details
Double Royal KushDetected and Quantified119.7 +/- 3.5 mg/g dry wt details
FLODetected and Quantified153 +/- 15.2 mg/g dry wt details
GabriolaDetected and Quantified0.951 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Grandaddy PurpleDetected and Quantified143 +/- 7.9 mg/g dry wt details
Green CrackDetected and Quantified203 +/- 23.3 mg/g dry wt details
Green Crack 2015Detected and Quantified171.7 +/- 13.3 mg/g dry wt details
Holy PowerDetected and Quantified215.3 +/- 20.4 mg/g dry wt details
Island HoneyDetected and Quantified0.703 mg/g dry wt
    • Jiamin Zheng, Yil...
details
JuanitaDetected and Quantified30.3 +/- 3.7 mg/g dry wt details
LavendarDetected and Quantified119.1 +/- 39.1 mg/g dry wt details
LavendarDetected and Quantified162.7 +/- 12.1 mg/g dry wt details
Lavendar Jones 2015Detected and Quantified165.3 +/- 28 mg/g dry wt details
Love LaceDetected and Quantified42 +/- 5.3 mg/g dry wt details
OracleDetected and Quantified170.2 +/- 4 mg/g dry wt details
Platinum BuffaloDetected and Quantified139 +/- 7.5 mg/g dry wt details
Platinum GorillaDetected and Quantified158 +/- 6 mg/g dry wt details
Platinum ScoutDetected and Quantified187 +/- 2.6 mg/g dry wt details
Purple Fat PieDetected and Quantified108.5 +/- 10.7 mg/g dry wt details
QuadraDetected and Quantified1.04 mg/g dry wt
    • Jiamin Zheng, Yil...
details
RomulinDetected and Quantified102.1 +/- 25.5 mg/g dry wt details
RXDetected and Quantified127.3 +/- 4.5 mg/g dry wt details
Sensi StarDetected and Quantified1.13 mg/g dry wt
    • Jiamin Zheng, Yil...
details
SkywalkerDetected and Quantified117.4 +/- 20.9 mg/g dry wt details
Sour WillieDetected and Quantified57.3 +/- 22.6 mg/g dry wt details
Tangerine DreamDetected and Quantified0.743 mg/g dry wt
    • Jiamin Zheng, Yil...
details
ThunderstruckDetected and Quantified59.4 +/- 6.3 mg/g dry wt details
Twisted VelvetDetected and Quantified124.7 +/- 12.9 mg/g dry wt details
Walker KushDetected and Quantified160.7 +/- 8.5 mg/g dry wt details
White WidowDetected and Quantified156.3 +/- 9.1 mg/g dry wt details
HMDB IDHMDB0014613
DrugBank IDDB00470
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031310
KNApSAcK IDC00002675
Chemspider ID15266
KEGG Compound IDC06972
BioCyc IDCPD-7172
BiGG IDNot Available
Wikipedia LinkTetrahydrocannabinol
METLIN IDNot Available
PubChem Compound16078
PDB IDNot Available
ChEBI ID66964
References
General References
  1. Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
  2. Koh WS, Crawford RB, Kaminski NE: Inhibition of protein kinase A and cyclic AMP response element (CRE)-specific transcription factor binding by delta9-tetrahydrocannabinol (delta9-THC): a putative mechanism of cannabinoid-induced immune modulation. Biochem Pharmacol. 1997 May 15;53(10):1477-84. doi: 10.1016/s0006-2952(97)82441-0. [PubMed:9260875 ]
  3. Little PJ, Martin BR: The effects of delta 9-tetrahydrocannabinol and other cannabinoids on cAMP accumulation in synaptosomes. Life Sci. 1991;48(12):1133-41. doi: 10.1016/0024-3205(91)90450-p. [PubMed:1848340 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5

Only showing the first 10 proteins. There are 12 proteins in total.