delta9-Tetrahydrocannabinol (CHEM002203)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:58 UTC
Update Date2026-05-14 16:39:47 UTC
Accession NumberCHEM002203
Identification
Common Namedelta9-Tetrahydrocannabinol
ClassSmall Molecule
DescriptionA psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound. Dronabinol is a synthetic form of delta-9-THC. THC has a very low solubility in water, but good solubility in most organic solvents, specifically lipids and alcohols. There has never been a documented human fatality solely from overdosing on tetrahydrocannabinol or cannabis in its natural form. However, numerous reports have suggested an association of cannabis smoking with an increased risk of myocardial infarction.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Analgesic
  • Analgesic, Non-Narcotic
  • Antiemetic
  • Cannabinoid Receptor Agonist
  • Drug
  • Ether
  • Hallucinogen
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Psychotropic Drug
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass314.462 g/mol
Monoisotopic Mass314.225 g/mol
CAS Registry Number1972-08-3
IUPAC Name(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional NameTHC
SMILES[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=C2C(O)=CC(CCCCC)=C1
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
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point200°C at 2.00E-02 mm Hg
Boiling Point200°C
Solubility2800 mg/L (at 23°C)
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0597-4090000000-670e40c1592b93325e44Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-6009000000-735bce5abc1be2637810Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-0219000000-1916f155ea706f1bfd78Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-05mx-3943000000-9b0e61162051930e030fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-052f-3920000000-06615e927292d6b78f04Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-006x-5900000000-c44a1196b35ae31ac75cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-00xu-7900000000-d06351b5900dfe483bd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-00tf-9600000000-14d6a1649ef828de05e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-00mo-9400000000-c1c5f46aa3925b6b440fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-00ou-9300000000-fec356cc420b4d525c37Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-016u-9200000000-295f54d67e0fa9512778Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, positivesplash10-0fvl-9200000000-92620f75edee11220267Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-053f-0980000000-c5e3986b120b13bf6cadSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00dr-0900000000-71e91d90ab20dda21879Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0002-9000000000-0c6530b23f4594b0199dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-03di-0910000000-13e75d88a02fafe0bbe2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-000j-0900000000-ae7ab2b9c0db456ba4d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00lr-0490000000-aebf4a983943679cba93Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-0910000000-13eb5c07bf46dbbbc6c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1239000000-dd0a437774bcd5f12cd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-6291000000-48cdeee605af2033e358Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9140000000-f6fc10c62a978b5bb9b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-1a8c2415357935328858Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0429000000-d0c2b14e825c4f547980Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01re-3930000000-3f6ef979ec17030832a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-2514638890974c4f71f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-f9f1dddf06624032e0deSpectrum
MSMass Spectrum (Electron Ionization)splash10-01pp-4792000000-06532e533cb7794b7c37Spectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityThe 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.
MetabolismHepatic Route of Elimination: Dronabinol and its biotransformation products are excreted in both feces and urine. Half Life: Alpha phase: approximately 4 hours; Beta phase: 25-36 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor 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 treatments
Minimum Risk LevelNot Available
Health EffectsThe heightened suggestibility and intensified emotions that hallucinogens create can worsen any pre-existing emotional problems. Physical effects of hallucinogen use include dilated pupils, sweating, insomnia, loss of appetite, tremors; and increased body temperature, heart rate and blood pressure.
SymptomsNot Available
TreatmentA 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. (8)
Concentrations
Not Available
DrugBank IDDB00470
HMDB IDHMDB0014613
FooDB IDFDB031310
Phenol Explorer IDNot Available
KNApSAcK IDC00002675
BiGG IDNot Available
BioCyc IDCPD-7172
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetrahydrocannabinol
Chemspider ID15266
ChEBI ID66964
PubChem Compound ID16078
Kegg Compound IDC06972
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Fabio E.S. SOUZA, Jason E. FIELD, Ming PAN, “INTERMEDIATE COMPOUNDS IN THE SYNTHESIS OF DRONABINOL.” U.S. Patent US20080312465, issued December 18, 2008.

MSDSLink
General References
1. Gregg JM, Small EW, Moore R, Raft D, Toomey TC: Emotional response to intravenous delta9tetrahydrocannabinol during oral surgery. J Oral Surg. 1976 Apr;34(4):301-13.
2. Schuel H, Burkman LJ: A tale of two cells: endocannabinoid-signaling regulates functions of neurons and sperm. Biol Reprod. 2005 Dec;73(6):1078-86. Epub 2005 Aug 24.
3. Zhu W, Friedman H, Klein TW: Delta9-tetrahydrocannabinol induces apoptosis in macrophages and lymphocytes: involvement of Bcl-2 and caspase-1. J Pharmacol Exp Ther. 1998 Aug;286(2):1103-9.
4. Zangen A, Solinas M, Ikemoto S, Goldberg SR, Wise RA: Two brain sites for cannabinoid reward. J Neurosci. 2006 May 3;26(18):4901-7.
5. Consroe P, Martin P, Eisenstein D: Anticonvulsant drug antagonism of delta9tetrahydrocannabinol-induced seizures in rabbits. Res Commun Chem Pathol Pharmacol. 1977 Jan;16(1):1-13.
6. Concheiro M, de Castro A, Quintela O, Cruz A, Lopez-Rivadulla M: Development and validation of a method for the quantitation of Delta9tetrahydrocannabinol in oral fluid by liquid chromatography electrospray-mass-spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Oct 25;810(2):319-24.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15190053
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16511162
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21310551
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21590520
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21671456
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21803011
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22260337
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22288893
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22305029
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22491047
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22553980
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22680341
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22722508
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22807156