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| Product Name: | AM 251 | | Synonyms: | AM 251;1-(2,4-DICHLOROPHENYL)-5-(4-IODOPHENYL)-4-METHYL-N-1-PIPERIDINYL-1 H-PYRAZOLE-3-CARBOXAMIDE;N-(PIPERIDIN-1-YL)-5-(4-IODOPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYL-1H-PYRAZOLE-3-CARBOXAMIDE;AM-251 ,99%;CS-985;AM 251 NEW;AM 251 (pharmaceutical);1H-Pyrazole-3-carboxamide, 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-1-piperidinyl- | | CAS: | 183232-66-8 | | MF: | C22H21Cl2IN4O | | MW: | 555.24 | | EINECS: | | | Product Categories: | Inhibitors;Cannabinoid receptor;Cannabinoid;Aromatics;Heterocycles;Cannabinoids | | Mol File: | 183232-66-8.mol |  |
| | AM 251 Chemical Properties |
| Melting point | 195-196℃ | | density | 1.65±0.1 g/cm3(Predicted) | | storage temp. | Store at RT | | solubility | DMSO: >10 mg/mL, soluble | | form | solid | | pka | 11.31±0.20(Predicted) | | color | white | | Stability: | Stable for 1 year as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | | 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 | Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCCCC4 | | CAS DataBase Reference | 183232-66-8 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2933.39.6190 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 4 |
| | AM 251 Usage And Synthesis |
| Description | AM251 is a cannabinoid 1 (CB1) receptor 1 antagonist. It binds to CB1 receptors in rat forebrain membrane preparations (Ki = 7.5 nM) and is selective over CB2 receptors in mouse spleen preparations (Ki = 2,290 nM) in radioligand binding assays. AM251 inhibits GTPγS binding induced by the CB receptor agonist CP 55,940 in HEK293 cells expressing human CB1 receptors (EC50 = 8 nM). AM251 (10 mg/kg) decreases immobility time in the forced swim test in wild-type but not CB1 receptor-deficient mice. It reduces fasting-induced food intake and body weight gain in mice when administered at a dose of 30 mg/kg. AM251 also induces GTPγS binding in HEK293 cells expressing the orphan receptor GPR55 (EC50 = 39 nM) and potentiates GABA-induced GABAA receptor currents (EC50 = 0.4 μM). It prevents TGF-β1-induced epithelial-to-mesenchymal transition (EMT), inhibits SMAD2/3 and p38 MAPK activation, and reduces the expression of EMT-related transcription factors in HK-2 renal tubule epithelial cells. AM251 induces cell cycle arrest at the G2/M phase and apoptosis in A375 human melanoma cells. | | Chemical Properties | White to Off-White Solid | | Uses | Inhibitor of CB1 receptors. AM 251is a biarylpyrazole compound which has been considered for many years as the prototypical cannabinoid (CB) receptor antagonist | | Uses | AM251, a CB1 cannabinoid receptor antagonist, has been used in a study to determine its interaction with hippocampal neurons to enhance spatial memory in mice. | | Definition | ChEBI: AM-251 is a carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor. It has a role as a CB1 receptor antagonist, an apoptosis inducer, an antidepressant and an antineoplastic agent. It is a member of pyrazoles, a dichlorobenzene, an organoiodine compound, an amidopiperidine and a carbohydrazide. | | Biological Activity | Potent CB 1 receptor antagonist (IC 50 = 8 nM, K i = 7.49 nM) that displays 306-fold selectivity over CB 2 receptors. Also potent GPR55 agonist (EC 50 = 39 nM). Also available as part of the Cannabinoid CB 1 Receptor Tocriset™ . | | Biochem/physiol Actions | AM251 is a CB1 cannabinoid receptor antagonist. | | storage | Room temperature | | References | [1] S.JOHN GATLEY . 123I-labeled AM251: a radioiodinated ligand which binds in vivo to mouse brain cannabinoid CB1 receptors[J]. European journal of pharmacology, 1996, 307 3: Pages 331-338. DOI:10.1016/0014-2999(96)00279-8
[2] S JOHN GATLEY . Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors[J]. Life sciences, 1997, 61 14: Pages PL191-PL197. DOI:10.1016/s0024-3205(97)00690-5
[3] PERTWEE R G. Inverse agonism and neutral antagonism at cannabinoid CB1 receptors[J]. Life sciences, 2005, 76 12: Pages 1307-1324. DOI:10.1016/j.lfs.2004.10.025
[4] L P SHEARMAN. Antidepressant-like and anorectic effects of the cannabinoid CB1 receptor inverse agonist AM251 in mice.[J]. Behavioural Pharmacology, 2003, 14 8: 573-582. DOI:10.1097/00008877-200312000-00001
[5] E RYBERG. The orphan receptor GPR55 is a novel cannabinoid receptor[J]. British Journal of Pharmacology, 2009, 152 7: 1092-1101. DOI:10.1038/sj.bjp.0707460 |
| | AM 251 Preparation Products And Raw materials |
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