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
References
1. Alexander SP. (2012)
So what do we call GPR18 now?.
Br. J. Pharmacol., 165 (8): 2411-3. [PMID:22014123]
2. Bayewitch M, Rhee MH, Avidor-Reiss T, Breuer A, Mechoulam R, Vogel Z. (1996)
(-)-Delta9-tetrahydrocannabinol antagonizes the peripheral cannabinoid receptor-mediated inhibition of adenylyl cyclase.
J. Biol. Chem., 271 (17): 9902-5. [PMID:8626625]
3. Bisogno T, Hanus L, De Petrocellis L, Tchilibon S, Ponde DE, Brandi I, Moriello AS, Davis JB, Mechoulam R, Di Marzo V. (2001)
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.
Br. J. Pharmacol., 134 (4): 845-52. [PMID:11606325]
4. Felder CC, Joyce KE, Briley EM, Mansouri J, Mackie K, Blond O, Lai Y, Ma AL, Mitchell RL. (1995)
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.
Mol. Pharmacol., 48 (3): 443-50. [PMID:7565624]
5. Jordt SE, Bautista DM, Chuang HH, McKemy DD, Zygmunt PM, Högestätt ED, Meng ID, Julius D. (2004)
Mustard oils and cannabinoids excite sensory nerve fibres through the TRP channel ANKTM1.
Nature, 427 (6971): 260-5. [PMID:14712238]
6. McHugh D, Page J, Dunn E, Bradshaw HB. (2012)
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
Br. J. Pharmacol., 165 (8): 2414-24. [PMID:21595653]
7. Qin N, Neeper MP, Liu Y, Hutchinson TL, Lubin ML, Flores CM. (2008)
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.
J. Neurosci., 28 (24): 6231-8. [PMID:18550765]
8. Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L, Breuer A, Mechoulam R. (1997)
Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase.
J. Med. Chem., 40 (20): 3228-33. [PMID:9379442]
9. Ryberg E, Larsson N, Sjögren S, Hjorth S, Hermansson NO, Leonova J, Elebring T, Nilsson K, Drmota T, Greasley PJ. (2007)
The orphan receptor GPR55 is a novel cannabinoid receptor.
Br. J. Pharmacol., 152 (7): 1092-101. [PMID:17876302]
10. Showalter VM, Compton DR, Martin BR, Abood ME. (1996)
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
J. Pharmacol. Exp. Ther., 278 (3): 989-99. [PMID:8819477]