Δ9-tetrahydrocannabinol   Click here for help

GtoPdb Ligand ID: 2424

Abbreviated name: THC
Synonyms: Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Approved drug PDB Ligand
Δ9-tetrahydrocannabinol is an approved drug (FDA (1985))
Compound class: Natural product
Comment: Δ9-tetrahydrocannabinol is the principle active ingredient derived from the cannabis plant (Cannabis sativa). Dronabinol is the INN for the pure, synthetically produced (-)-trans-Δ9-tetrahydrocannabinol isomer of tetrahydrocannabinol (shown here).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: delta-9-tetrahydrocannabinol

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 0
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 29.46
Molecular weight 314.22
XLogP 6.47
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCc1cc(O)c2c(c1)OC(C1C2C=C(C)CC1)(C)C
Isomeric SMILES CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C
InChI 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 CYQFCXCEBYINGO-IAGOWNOFSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of anorexia in patients with AIDS, and treatment of nausea and vomiting associated with cancer chemotherapy in patients who have not reposnded to conventional antiemetic treatments. Clinical formulations of dronabinol are available in capsule form (Marinol®), and as of July 2016 (with US FDA apporval), as an oral solution (Syndros®).
Tetrahydrocannabinol, in a drug mixture containing cannabidiol (Sativex®, administered as an oromucosal spray), may also be used (in countries including the UK, Spain, Italy and Germany) to improve moderate to severe spastic symptoms in patients with multiple sclerosis (MS), and who have responded poorly to other anti-spasticity medications. The ability of dronabinol to reduce agitation in patients with Alzheimer's disease is being evaluated in clinical studies.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism of action of THC is not completely understood. CB1 receptor agonist activity inhibits cyclic AMP production in areas of the central nervous system that mediate pain, memory, and other key functions, and is at least partially responsible for the physiological effects of cannabinoids. In addition, cannabidiol has been shown to stimulate vanilloid pain receptors (TRPVs), and to modulate cellular uptake and enzymatic hydrolysis of endogenous anandamide, effects which may contribute towards the pharmacological effects of cannabidiol [3].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02792257 Trial of Dronabinol Adjunctive Treatment of Agitation in Alzheimer's Disease Phase 2 Interventional Johns Hopkins University 4
NCT05239390 SCI-110 for Alzheimer Disease and Agitation Phase 2 Interventional The Israeli Medical Center for Alzheimer's
NCT05612711 Dronabinol for Agitation in Dementia Crossover Trial Phase 2 Interventional Ralph H. Johnson VA Medical Center
NCT05543681 Clinical Trial on Agitation in Alzheimer's Dementia Phase 2 Interventional IGC Pharma, LLC
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com