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 or derivative
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 CDK toolkit. 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
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.

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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
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB1 receptor Primary target of this compound Hs Agonist Partial agonist 7.3 – 7.4 pKi - 4,10
⤷ pKi 7.3 – 7.4 [4,10]
CB2 receptor Hs Agonist Partial agonist 7.1 – 7.5 pKi - 2,4,8,10
⤷ pKi 7.1 – 7.5 [2,4,8,10]
GPR55 Hs Agonist Agonist 8.1 pEC50 - 9
⤷ pEC50 8.1 (EC50 8x10-9 M) [9]
GPR18 Hs Agonist Full agonist 6.0 pEC50 - 1,6
⤷ pEC50 6.0 (EC50 9.6x10-7 M) [1,6]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
glycine receptor α2 subunit Hs Allosteric modulator Potentiation ~6.0 pEC50 -
⤷ pEC50 ~6.0 (EC50 ~1x10-6 M) ~230% potentiation
glycine receptor α1 subunit Hs Allosteric modulator Potentiation ~5.5 pEC50 -
⤷ pEC50 ~5.5 (EC50 ~3x10-6 M) ~1500% potentiation
glycine receptor α3 subunit Hs Allosteric modulator Potentiation ~5.3 pEC50 -
⤷ pEC50 ~5.3 (EC50 ~5x10-6 M) ~1500% potentiation
TRPA1 Hs Activator Agonist 4.9 pEC50 - 5
⤷ pEC50 4.9 (EC50 1.259x10-5 M) non-covalent [5]
Voltage: -60.0 mV
TRPV2 Rn Activator Activation 4.8 pEC50 - 7
⤷ pEC50 4.8 (EC50 1.4x10-5 M) [7]
TRPM8 Hs Channel blocker - - - -
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Targets where the ligand is described in the comment field
Target Comment
TRPM8 Cannabidiol and Δ9-tetrahydrocannabinol are examples of cannabinoid activators. TRPM8 is insensitive to ruthenium red. Icilin requires intracellular Ca2+ for full agonist activity.
Ligand mentioned in the following text fields
Cannabinoid receptors overview
GPR18, GPR55 and GPR119 comments
Sphingolipid Δ4-desaturase comments