| Identification | Back Directory | [Name]
1-(2,4-DICHLOROPHENYL)-5-(4-IODOPHENYL)-4-METHYL-N-4-MORPHOLINYL-1H-PYRAZOLE-3-CARBOXAMIDE | [CAS]
202463-68-1 | [Synonyms]
AM 281
CS-1127
AM-281 ,99%
AM281;AM-281
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-morpholin-4-ylpyrazole-3-carboxamide
1-(2,4-DICHLOROPHENYL)-5-(4-IODOPHENYL)-4-METHYL-N-4-MORPHOLINYL-1H-PYRAZOLE-3-CARBOXAMIDE
1H-Pyrazole-3-carboxamide,1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-4-morpholinyl-
1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-4-morpholinyl-1H-pyrazole-3-carboxamide AM 281 | [Molecular Formula]
C21H19Cl2IN4O2 | [MDL Number]
MFCD01861180 | [MOL File]
202463-68-1.mol | [Molecular Weight]
557.21 |
| Chemical Properties | Back Directory | [density ]
1.70±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: >6 mg/mL
| [form ]
solid
| [pka]
10.76±0.20(Predicted) | [color ]
white
| [InChI]
1S/C21H19Cl2IN4O2/c1-13-19(21(29)26-27-8-10-30-11-9-27)25-28(18-7-4-15(22)12-17(18)23)20(13)14-2-5-16(24)6-3-14/h2-7,12H,8-11H2,1H3,(H,26,29) | [InChIKey]
AJFFBPZYXRNAIC-UHFFFAOYSA-N | [SMILES]
Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCOCC4 |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25-36/37/38 | [Safety Statements ]
26-36/37/39-45 | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
AM281 is a potent and selective central cannabinoid (CB1) receptor antagonist/inverse agonist (Kis = 12 nM and 4,200 nM for CB1 and CB2, respectively). Structurally, it is an analog of the CB1 inverse agonist rimonabant . It has no effect on the vanilloid TRPV1 receptor. AM281 has been used to evaluate the potential effects of compounds at CB1. It has also been used to study the membrane localization and cycling of CB1. | [Uses]
AM 281 acts as a potential CB1 selective receptor cannabinoid antagonist. | [Definition]
ChEBI: 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(4-morpholinyl)-3-pyrazolecarboxamide is a member of pyrazoles and a ring assembly. | [Biological Activity]
Potent, selective CB 1 cannabinoid receptor antagonist/inverse agonist (K i values are 12 and 4200 nM for CB 1 and CB 2 receptors respectively). Increases locomotor activity following systemic administration in vivo . Analog of SR141716A (K i = 14 nM). | [storage]
+4°C (desiccate) | [References]
[1]. lan r, gatley j, lu q, et al. design and synthesis of the cb1 selective cannabinoid antagonist am281: a potential human spect ligand. aaps pharmsci, 1999, 1(2): e4.
[2]. gatley sj, lan r, volkow nd, et al. imaging the brain marijuana receptor: development of a radioligand that binds to cannabinoid cb1 receptors in vivo. j neurochem, 1998, 70(1): 417-423.
[3]. vaseghi g, rabbani m, hajhashemi v. the cb(1) receptor antagonist, am281, improves recognition loss induced by naloxone in morphine withdrawal mice. basic clin pharmacol toxicol, 2012, 111(3): 161-165. |
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