AM251

• CAT Number: I002375
• CAS Number: 183232-66-8
• Molecular Formula: C22H21Cl2IN4O
• Molecular Weight: 555.2
• Purity: ≥95%
• Synonyms: 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
• Target: Cannabinoid Receptor
• Solubility: 10 mM in DMSO
• Storage: 3 years -20C powder
• 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)
• InChIKey: BUZAJRPLUGXRAB-UHFFFAOYSA-N
• SMILES: Ic1ccc(cc1)c1c(C)c(nn1c1ccc(Cl)cc1Cl)C(=O)NN1CCCCC1

AM251 is a potent CB1 receptor antagonist (IC50 = 8 nM, Ki = 7.49 nM) that displays 306-fold selectivity over CB2 receptors; also potent GPR55 agonist (EC50 = 39 nM).IC50 value:Target: CB1 receptor antagonistin vitro: In in vitro binding assays with mouse hippocampal membranes, tetrahydrocannabinol inhibited binding of [123I]AM251 with an IC50 value of about 700 nM, compared with about 0.2 nM for SR141716A [1]. Kd values were lower for [123I]AM251 (0.23-0.62 nM) than for [3H]CP 55,940 (1.3-4 nM). CP 55,940 and SR141716A increased dissociation of [123I]AM251 from binding sites in mouse cerebellar homogenates to a similar extent [2].

Reference

1:AM251 Suppresses Epithelial-Mesenchymal Transition of Renal Tubular Epithelial Cells. Yoshinaga T, Uwabe K, Naito S, Higashino K, Nakano T, Numata Y, Kihara A.PLoS One. 2016 Dec 9;11(12):e0167848. doi: 10.1371/journal.pone.0167848. eCollection 2016. PMID: 27936102 Free PMC Article2:Interactive effects of AM251 and baclofen on synaptic plasticity in the rat dentate gyrus. Nazari M, Komaki A, Salehi I, Sarihi A, Shahidi S, Komaki H, Ganji A.Brain Res. 2016 Nov 15;1651:53-60. doi: 10.1016/j.brainres.2016.09.029. Epub 2016 Sep 20. PMID: 27663967 3:Concentration, population, and context-dependent effects of AM251 in zebrafish. Tran S, Chatterjee D, Facciol A, Gerlai R.Psychopharmacology (Berl). 2016 Apr;233(8):1445-54. doi: 10.1007/s00213-016-4240-y. Epub 2016 Feb 16. PMID: 26883874 4:Prevention of drug priming- and cue-induced reinstatement of MDMA-seeking behaviors by the CB1 cannabinoid receptor antagonist AM251. Nawata Y, Kitaichi K, Yamamoto T.Drug Alcohol Depend. 2016 Mar 1;160:76-81. doi: 10.1016/j.drugalcdep.2015.12.016. Epub 2015 Dec 30. PMID: 26796595 5:AM251 induces apoptosis and G2/M cell cycle arrest in A375 human melanoma cells. Carpi S, Fogli S, Romanini A, Pellegrino M, Adinolfi B, Podestà A, Costa B, Da Pozzo E, Martini C, Breschi MC, Nieri P.Anticancer Drugs. 2015 Aug;26(7):754-62. doi: 10.1097/CAD.0000000000000246. PMID: 25974027 6:Chronic administration of AM251 improves albuminuria and renal tubular structure in obese rats. Jenkin KA, O/’Keefe L, Simcocks AC, Grinfeld E, Mathai ML, McAinch AJ, Hryciw DH.J Endocrinol. 2015 May;225(2):113-24. doi: 10.1530/JOE-15-0004. Epub 2015 Mar 24. PMID: 25804605 Free Article7:The cannabinoid receptor antagonist AM251 increases paraoxon and chlorpyrifos oxon toxicity in rats. Liu J, Pope C.Neurotoxicology. 2015 Jan;46:12-8. doi: 10.1016/j.neuro.2014.11.001. Epub 2014 Nov 20. PMID: 25447325 Free PMC Article8:Systemic or intra-amygdala infusion of an endocannabinoid CB1 receptor antagonist AM251 blocked propofol-induced anterograde amnesia. Ren Y, Wang J, Xu PB, Xu YJ, Miao CH.Neurosci Lett. 2015 Jan 1;584:287-91. doi: 10.1016/j.neulet.2014.11.001. Epub 2014 Nov 6. PMID: 25445359 9:Cannabinoid receptor type 1 antagonist, AM251, attenuates mechanical allodynia and thermal hyperalgesia after burn injury. Ueda M, Iwasaki H, Wang S, Murata E, Poon KY, Mao J, Martyn JA.Anesthesiology. 2014 Dec;121(6):1311-9. doi: 10.1097/ALN.0000000000000422. PMID: 25188001 Free PMC Article10:The CB1 receptor antagonist AM251 impairs reconsolidation of pavlovian fear memory in the rat basolateral amygdala. Ratano P, Everitt BJ, Milton AL.Neuropsychopharmacology. 2014 Oct;39(11):2529-37. doi: 10.1038/npp.2014.103. Epub 2014 May 7. PMID: 24801769 Free PMC Article