Δ9-tetrahydrocannabinol   

GtoPdb Ligand ID: 2424

Abbreviated name: THC
Synonyms: Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Δ9-tetrahydrocannabinol is an approved drug (FDA (1985))
Comment: Δ9-tetrahydrocannabinol is the principle active ingredient derived from the cannabis plant (Cannabis sativa). Dronabinol is the INN for the pure, synthetically produced (-)-trans9-tetrahydrocannabinol isomer of tetrahydrocannabinol (shown here).
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2D Structure
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Physico-chemical Properties
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
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
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB1 receptor 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
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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 - - - -
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields