AM251   Click here for help

GtoPdb Ligand ID: 3317

Synonyms: AM 251 | AM-251
Compound class: Synthetic organic
Comment: AM251 is a CB1 receptor antagonist/inverse agonist. Experiments in rats indicate that AM251 has potential as a prophylactic antidote to the cannabinoid receptor mediated, often life-threatening, side-effects that are an increasingly common cause for concern in individuals taking highly potent synthetic cannabinoids recreationally [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 49.64
Molecular weight 554.01
XLogP 6.58
No. Lipinski's rules broken 1
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Canonical SMILES Ic1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
Isomeric SMILES Ic1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
InChI InChI=1S/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
1. Henstridge CM, Balenga NA, Schröder R, Kargl JK, Platzer W, Martini L, Arthur S, Penman J, Whistler JL, Kostenis E, Waldhoer M, Irving AJ. (2010)
GPR55 ligands promote receptor coupling to multiple signalling pathways.
Br J Pharmacol, 160 (3): 604-14. [PMID:20136841]
2. Kapur A, Zhao P, Sharir H, Bai Y, Caron MG, Barak LS, Abood ME. (2009)
Atypical responsiveness of the orphan receptor GPR55 to cannabinoid ligands.
J Biol Chem, 284 (43): 29817-27. [PMID:19723626]
3. Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, Pertwee R, Makriyannis A. (1999)
Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists.
J Med Chem, 42 (4): 769-76. [PMID:10052983]
4. 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]
5. Pryce G, Baker D. (2017)
Antidote to cannabinoid intoxication: the CB1 receptor inverse agonist, AM251, reverses hypothermic effects of the CB1 receptor agonist, CB-13, in mice.
Br J Pharmacol, 174 (21): 3790-3794. [PMID:28800377]
6. 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]