T3DB: delta9-Tetrahydrocannabinol

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Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (3)XML

Targets (3)

Record Information

Version

2.0

Creation Date

2009-07-21 20:26:58 UTC

Update Date

2014-12-24 20:25:51 UTC

Accession Number

T3D2801

Identification

Common Name

delta9-Tetrahydrocannabinol

Class

Small Molecule

Description

A 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Formula

C₂₁H₃₀O₂

Average Molecular Mass

314.462 g/mol

Monoisotopic Mass

314.225 g/mol

CAS Registry Number

1972-08-3

IUPAC Name

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

Traditional Name

THC

SMILES

[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21

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 Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyketide (CHEBI:66964 )
diterpenoid (CHEBI:66964 )
phytocannabinoid (CHEBI:66964 )
benzochromene (CHEBI:66964 )
Cannabinoids (C06972 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	200°C at 2.00E-02 mm Hg
Boiling Point	200°C
Solubility	2800 mg/L (at 23°C)
LogP	5.648

Predicted Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	7.29	ALOGPS
logP	5.94	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.73 m³·mol⁻¹	ChemAxon
Polarizability	38.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0597-4090000000-670e40c1592b93325e44	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-6009000000-735bce5abc1be2637810	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014i-0219000000-1916f155ea706f1bfd78	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-05mx-3943000000-9b0e61162051930e030f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, positive	splash10-052f-3920000000-06615e927292d6b78f04	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, positive	splash10-006x-5900000000-c44a1196b35ae31ac75c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 31V, positive	splash10-00xu-7900000000-d06351b5900dfe483bd6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 37V, positive	splash10-00tf-9600000000-14d6a1649ef828de05e3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 43V, positive	splash10-00mo-9400000000-c1c5f46aa3925b6b440f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 50V, positive	splash10-00ou-9300000000-fec356cc420b4d525c37	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 59V, positive	splash10-016u-9200000000-295f54d67e0fa9512778	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, positive	splash10-0fvl-9200000000-92620f75edee11220267	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-053f-0980000000-c5e3986b120b13bf6cad	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-00dr-0900000000-71e91d90ab20dda21879	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-0002-9000000000-0c6530b23f4594b0199d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-03di-0910000000-13e75d88a02fafe0bbe2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-000j-0900000000-ae7ab2b9c0db456ba4d4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-00lr-0490000000-aebf4a983943679cba93	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-004i-0910000000-13eb5c07bf46dbbbc6c3	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1239000000-dd0a437774bcd5f12cd9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-6291000000-48cdeee605af2033e358	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9140000000-f6fc10c62a978b5bb9b0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-1a8c2415357935328858	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0429000000-d0c2b14e825c4f547980	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01re-3930000000-3f6ef979ec17030832a8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-2514638890974c4f71f3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009000000-f9f1dddf06624032e0de	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01pp-4792000000-06532e533cb7794b7c37	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

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.

Metabolism

Hepatic 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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 treatments

Minimum Risk Level

Not Available

Health Effects

The 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.

Symptoms

Not Available

Treatment

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. (8)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Marinol

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Marinol

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.

MSDS

Link

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Drugs.com [Link]
RxList: The Internet Drug Index (2009). [Link]

Gene Regulation

Up-Regulated Genes

Gene	Gene Symbol	Gene ID	Interaction	Chromosome	Details

Down-Regulated Genes

Gene	Gene Symbol	Gene ID	Interaction	Chromosome	Details

Targets

Target Details

1. Cannabinoid receptor 2

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

Type	Value	Assay Type	Assay Source
Inhibitory	0.0033 uM	Not Available	BindingDB 50007391
Inhibitory	0.024 uM	Not Available	BindingDB 50007391
Inhibitory	0.025 uM	Not Available	BindingDB 50007391
Inhibitory	0.036 uM	Not Available	BindingDB 50007391
Inhibitory	0.041 uM	Not Available	BindingDB 50007391
IC50	0.0095 uM	Not Available	BindingDB 50007391

References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Target Details

2. Cannabinoid receptor 1

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

Type	Value	Assay Type	Assay Source
Inhibitory	0.0029 uM	Not Available	BindingDB 50007391
Inhibitory	0.01 uM	Not Available	BindingDB 50007391
Inhibitory	0.017 uM	Not Available	BindingDB 50007391
Inhibitory	0.0285 uM	Not Available	BindingDB 50007391
Inhibitory	0.04 uM	Not Available	BindingDB 50007391
Inhibitory	0.041 uM	Not Available	BindingDB 50007391
IC50	0.0028 uM	Not Available	BindingDB 50007391

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Target Details

3. G-protein coupled receptor 55

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

Type	Value	Assay Type	Assay Source
IC50	14.2 uM	Not Available	BindingDB 50007391

References

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 ]

delta9-Tetrahydrocannabinol (T3D2801)

Structure for T3D2801: delta9-Tetrahydrocannabinol

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References