Record Information
Version2.0
Creation Date2009-07-21 20:26:58 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2801
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.
Compound Type
  • Analgesic
  • Analgesic, Non-Narcotic
  • Antiemetic
  • Cannabinoid Receptor Agonist
  • Drug
  • Ether
  • Hallucinogen
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Psychotropic Drug
Chemical Structure
Thumb
Synonyms
Synonym
(-)- delta 9-Tetrahydrocannabinol
(-)-delta 1-Tetrahydrocannabinol
(-)-delta 9-THC
(-)-delta 9-trans-Tetrahydrocannabinol
(-)-delta9-trans-Tetrahydrocannabinol
(-)-trans-delta 1-Tetrahydrocannabinol
(-)-trans-delta 9-Tetrahydrocannabinol
(-)-trans-delta 9-THC
(L)-delta 1-Tetrahydrocannabinol
1-trans-delta 9-Tetrahydrocannabinol
1-trans-delta-9-Tetrahydrocannabinol
14C-delta 1-Tetrahydrocannabinol
3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-ol
6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
delta 1-Tetrahydrocannabinol
delta 1-THC
delta 9-Tetrahydrocannabinol
delta 9-Thc
delta 9-THC
delta 9-trans-Tetrahydrocannabinol
delta(1)-Tetrahydrocannabinol
delta(9)-THC
delta-9-Tetrahydrocannabinol
delta-9-THC
Dronabinol
Dronabinolum
Exocyclic delta (9)(11)-Tetrahydrocannabiol
L-delta 1-trans-Tetrahydrocannabinol
L-trans-delta 9-Tetrahydrocannabinol
Marinol
Primolut
Tetrahydrocannabinol
THC
trans-delta (-)-9-Tetrahydrocannabinol
trans-delta 9-Tetrahydrocannabinol
Δ9-tetrahydrocannabinol
δ9-Tetrahydrocannabinol
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=CC(CCCCC)=CC(O)=C21
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 KeyInChIKey=CYQFCXCEBYINGO-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)
LogP5.648
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0597-4090000000-670e40c1592b93325e442017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-6009000000-735bce5abc1be26378102017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-0219000000-1916f155ea706f1bfd782020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-05mx-3943000000-9b0e61162051930e030f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-052f-3920000000-06615e927292d6b78f042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-006x-5900000000-c44a1196b35ae31ac75c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-00xu-7900000000-d06351b5900dfe483bd62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-00tf-9600000000-14d6a1649ef828de05e32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-00mo-9400000000-c1c5f46aa3925b6b440f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-00ou-9300000000-fec356cc420b4d525c372020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-016u-9200000000-295f54d67e0fa95127782020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, positivesplash10-0fvl-9200000000-92620f75edee112202672020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-053f-0980000000-c5e3986b120b13bf6cad2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00dr-0900000000-71e91d90ab20dda218792020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0002-9000000000-0c6530b23f4594b0199d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-03di-0910000000-13e75d88a02fafe0bbe22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-000j-0900000000-ae7ab2b9c0db456ba4d42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00lr-0490000000-aebf4a983943679cba932020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-0910000000-13eb5c07bf46dbbbc6c32020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1239000000-dd0a437774bcd5f12cd92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-6291000000-48cdeee605af2033e3582016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9140000000-f6fc10c62a978b5bb9b02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-1a8c24153579353288582016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0429000000-d0c2b14e825c4f5479802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01re-3930000000-3f6ef979ec17030832a82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-2514638890974c4f71f32021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-f9f1dddf06624032e0de2021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-01pp-4792000000-06532e533cb7794b7c372014-09-20View Spectrum
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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00470
HMDB IDHMDB41865
PubChem Compound ID2978
ChEMBL IDCHEMBL465
ChemSpider ID2872
KEGG IDC06972
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMarinol
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMarinol
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. [1062533 ]
  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. [16120829 ]
  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. [9694974 ]
  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. [16672664 ]
  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. [841172 ]
  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. [15380731 ]
  7. Drugs.com [Link]
  8. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Cannabinoid receptor activity
Specific Function:
Heterotrimeric G protein-coupled receptor for endocannabinoid 2-arachidonoylglycerol mediating inhibition of adenylate cyclase. May function in inflammatory response, nociceptive transmission and bone homeostasis.
Gene Name:
CNR2
Uniprot ID:
P34972
Molecular Weight:
39680.275 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0033 uMNot AvailableBindingDB 50007391
Inhibitory0.024 uMNot AvailableBindingDB 50007391
Inhibitory0.025 uMNot AvailableBindingDB 50007391
Inhibitory0.036 uMNot AvailableBindingDB 50007391
Inhibitory0.041 uMNot AvailableBindingDB 50007391
IC500.0095 uMNot AvailableBindingDB 50007391
References
  1. Davis M, Maida V, Daeninck P, Pergolizzi J: The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer. 2007 Jan;15(1):63-71. Epub 2006 Dec 1. [17139494 ]
  2. Pertwee RG: Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411. doi: 10.1111/j.1476-5381.2008.00048.x. [19226257 ]
  3. Gutierrez M, Pereira AR, Debonsi HM, Ligresti A, Di Marzo V, Gerwick WH: Cannabinomimetic lipid from a marine cyanobacterium. J Nat Prod. 2011 Oct 28;74(10):2313-7. doi: 10.1021/np200610t. Epub 2011 Oct 14. [21999614 ]
  4. Kai H, Morioka Y, Tomida M, Takahashi T, Hattori M, Hanasaki K, Koike K, Chiba H, Shinohara S, Kanemasa T, Iwamoto Y, Takahashi K, Yamaguchi Y, Baba T, Yoshikawa T, Takenaka H: 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: orally bioavailable compounds. Bioorg Med Chem Lett. 2007 Jul 15;17(14):3925-9. Epub 2007 May 3. [17531479 ]
  5. Cheng YX, Pourashraf M, Luo X, Srivastava S, Walpole C, Salois D, St-Onge S, Payza K, Lessard E, Yu XH, Tomaszewski MJ: gamma-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration. Bioorg Med Chem Lett. 2012 Feb 15;22(4):1619-24. doi: 10.1016/j.bmcl.2011.12.124. Epub 2012 Jan 4. [22284817 ]
  6. Krishnamurthy M, Ferreira AM, Moore BM 2nd: Synthesis and testing of novel phenyl substituted side-chain analogues of classical cannabinoids. Bioorg Med Chem Lett. 2003 Oct 20;13(20):3487-90. [14505654 ]
  7. Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, Martin BR, Bramblett RD, Reggio PH: Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor. J Med Chem. 1996 Sep 27;39(20):3875-7. [8831752 ]
  8. Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK: Novel cannabinol probes for CB1 and CB2 cannabinoid receptors. J Med Chem. 2000 Oct 5;43(20):3778-85. [11020293 ]
  9. Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR: 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett. 2005 Sep 15;15(18):4110-3. [16005223 ]
  10. Huffman JW, Thompson AL, Wiley JL, Martin BR: Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg Med Chem. 2008 Jan 1;16(1):322-35. Epub 2007 Sep 22. [17919913 ]
  11. Burdick D, DeOrazio R, Guzzo P, Habershaw A, Helle M, Paul B, Wolf M: Synthesis and structure-activity relationship of substitutions at the C-1 position of Delta9-tetrahydrocannabinol. Bioorg Med Chem Lett. 2010 Feb 15;20(4):1424-6. doi: 10.1016/j.bmcl.2009.12.092. Epub 2010 Jan 4. [20079638 ]
  12. Huffman JW, Hepburn SA, Reggio PH, Hurst DP, Wiley JL, Martin BR: Synthesis and pharmacology of 1-methoxy analogs of CP-47,497. Bioorg Med Chem. 2010 Aug 1;18(15):5475-82. doi: 10.1016/j.bmc.2010.06.054. Epub 2010 Jun 22. [20621488 ]
  13. Huffman JW, Hepburn SA, Lyutenko N, Thompson AL, Wiley JL, Selley DE, Martin BR: 1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Delta(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor. Bioorg Med Chem. 2010 Nov 15;18(22):7809-15. doi: 10.1016/j.bmc.2010.09.061. Epub 2010 Sep 29. [20943404 ]
  14. Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW: Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents. Bioorg Med Chem. 2012 Mar 15;20(6):2067-81. doi: 10.1016/j.bmc.2012.01.038. Epub 2012 Jan 30. [22341572 ]
  15. Page D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, Wei Z, Woo S, Luo X, Cheng YX, Yang H, Srivastava S, Zhou F, Brown W, Tomaszewski M, Walpole C, Hodzic L, St-Onge S, Godbout C, Salois D, Payza K: Novel benzimidazole derivatives as selective CB2 agonists. Bioorg Med Chem Lett. 2008 Jul 1;18(13):3695-700. doi: 10.1016/j.bmcl.2008.05.073. Epub 2008 May 22. [18522867 ]
  16. Rajasekaran M, Brents LK, Franks LN, Moran JH, Prather PL: Human metabolites of synthetic cannabinoids JWH-018 and JWH-073 bind with high affinity and act as potent agonists at cannabinoid type-2 receptors. Toxicol Appl Pharmacol. 2013 Jun 1;269(2):100-8. doi: 10.1016/j.taap.2013.03.012. Epub 2013 Mar 26. [23537664 ]
General Function:
Drug binding
Specific Function:
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding.
Gene Name:
CNR1
Uniprot ID:
P21554
Molecular Weight:
52857.365 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0029 uMNot AvailableBindingDB 50007391
Inhibitory0.01 uMNot AvailableBindingDB 50007391
Inhibitory0.017 uMNot AvailableBindingDB 50007391
Inhibitory0.0285 uMNot AvailableBindingDB 50007391
Inhibitory0.04 uMNot AvailableBindingDB 50007391
Inhibitory0.041 uMNot AvailableBindingDB 50007391
IC500.0028 uMNot AvailableBindingDB 50007391
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Pryce G, Giovannoni G, Baker D: Mifepristone or inhibition of 11beta-hydroxylase activity potentiates the sedating effects of the cannabinoid receptor-1 agonist Delta(9)-tetrahydrocannabinol in mice. Neurosci Lett. 2003 May 1;341(2):164-6. [12686391 ]
  4. Tsai SJ, Wang YC, Hong CJ: Association study of a cannabinoid receptor gene (CNR1) polymorphism and schizophrenia. Psychiatr Genet. 2000 Sep;10(3):149-51. [11204352 ]
  5. Gutierrez M, Pereira AR, Debonsi HM, Ligresti A, Di Marzo V, Gerwick WH: Cannabinomimetic lipid from a marine cyanobacterium. J Nat Prod. 2011 Oct 28;74(10):2313-7. doi: 10.1021/np200610t. Epub 2011 Oct 14. [21999614 ]
  6. Page D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, Wei Z, Woo S, Luo X, Cheng YX, Yang H, Srivastava S, Zhou F, Brown W, Tomaszewski M, Walpole C, Hodzic L, St-Onge S, Godbout C, Salois D, Payza K: Novel benzimidazole derivatives as selective CB2 agonists. Bioorg Med Chem Lett. 2008 Jul 1;18(13):3695-700. doi: 10.1016/j.bmcl.2008.05.073. Epub 2008 May 22. [18522867 ]
  7. Cheng YX, Pourashraf M, Luo X, Srivastava S, Walpole C, Salois D, St-Onge S, Payza K, Lessard E, Yu XH, Tomaszewski MJ: gamma-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration. Bioorg Med Chem Lett. 2012 Feb 15;22(4):1619-24. doi: 10.1016/j.bmcl.2011.12.124. Epub 2012 Jan 4. [22284817 ]
  8. Kai H, Morioka Y, Tomida M, Takahashi T, Hattori M, Hanasaki K, Koike K, Chiba H, Shinohara S, Kanemasa T, Iwamoto Y, Takahashi K, Yamaguchi Y, Baba T, Yoshikawa T, Takenaka H: 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: orally bioavailable compounds. Bioorg Med Chem Lett. 2007 Jul 15;17(14):3925-9. Epub 2007 May 3. [17531479 ]
  9. Krishnamurthy M, Ferreira AM, Moore BM 2nd: Synthesis and testing of novel phenyl substituted side-chain analogues of classical cannabinoids. Bioorg Med Chem Lett. 2003 Oct 20;13(20):3487-90. [14505654 ]
  10. Burdick D, DeOrazio R, Guzzo P, Habershaw A, Helle M, Paul B, Wolf M: Synthesis and structure-activity relationship of substitutions at the C-1 position of Delta9-tetrahydrocannabinol. Bioorg Med Chem Lett. 2010 Feb 15;20(4):1424-6. doi: 10.1016/j.bmcl.2009.12.092. Epub 2010 Jan 4. [20079638 ]
  11. Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, Martin BR, Bramblett RD, Reggio PH: Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor. J Med Chem. 1996 Sep 27;39(20):3875-7. [8831752 ]
  12. Singer M, Ryan WJ, Saha B, Martin BR, Razdan RK: Potent cyano and carboxamido side-chain analogues of 1', 1'-dimethyl-delta8-tetrahydrocannabinol. J Med Chem. 1998 Oct 22;41(22):4400-7. [9784115 ]
  13. Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK: Novel cannabinol probes for CB1 and CB2 cannabinoid receptors. J Med Chem. 2000 Oct 5;43(20):3778-85. [11020293 ]
  14. Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW: Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents. Bioorg Med Chem. 2012 Mar 15;20(6):2067-81. doi: 10.1016/j.bmc.2012.01.038. Epub 2012 Jan 30. [22341572 ]
General Function:
G-protein coupled receptor activity
Specific Function:
May be involved in hyperalgesia associated with inflammatory and neuropathic pain (By similarity). Receptor for L-alpha-lysophosphatidylinositol (LPI). LPI induces Ca(2+) release from intracellular stores via the heterotrimeric G protein GNA13 and RHOA. Putative cannabinoid receptor. May play a role in bone physiology by regulating osteoclast number and function.
Gene Name:
GPR55
Uniprot ID:
Q9Y2T6
Molecular Weight:
36637.12 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC5014.2 uMNot AvailableBindingDB 50007391
References
  1. Rempel V, Volz N, Glaser F, Nieger M, Brase S, Muller CE: Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold. J Med Chem. 2013 Jun 13;56(11):4798-810. doi: 10.1021/jm4005175. Epub 2013 May 30. [23679955 ]