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Submit ReviewSR 144528
Description: High affinity and selective CB2 inverse agonist
Chemical Name: 5-(4-Chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]-1H-pyrazole-3-carboxamide
Purity: ≥98% (HPLC)
Biological Activity
High affinity and selective CB2 inverse agonist (Ki = 0.6 nM). Exhibits >700-fold selectivity for CB2 over CB1 receptors. Blocks the effects of CP 55,940 (Cat. No. 0949) on forskolin-sensitive adenylyl cyclase activity and MAPK in CHO cells expressing CB2 receptors. Also blocks CP 55,940-induced B-cell activation. Orally bioavailable.
Technical Data
| M. Wt | 476.05 |
| Formula | C29H34ClN3O |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 192703-06-3 |
| PubChem ID | 3081355 |
| InChI Key | SUGVYNSRNKFXQM-XRHWURSXSA-N |
| Smiles | C[C@]1(C2)[C@H](NC(C3=NN(CC4=CC=C(C)C=C4)C(C5=CC=C(Cl)C(C)=C5)=C3)=O)C(C)(C)[C@@H]2CC1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 47.6 | 100 | |
| ethanol | 47.6 | 100 |
Preparing Stock Solutions
The following data is based on the product molecular weight 476.05. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.1 mL | 10.5 mL | 21.01 mL |
| 5 mM | 0.42 mL | 2.1 mL | 4.2 mL |
| 10 mM | 0.21 mL | 1.05 mL | 2.1 mL |
| 50 mM | 0.04 mL | 0.21 mL | 0.42 mL |
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References
References are publications that support the biological activity of the product.
Rinaldi-Carmona et al (1998) SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. J.Pharmacol.Exp.Ther. 284 644 PMID: 9454810
Kotsikorou et al (2013) The importance of hydrogen bonding and aromatic stacking to the affinity and efficacy of cannabinoid receptor CB2 antagonist, 5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimeth J.Med.Chem. 56 6593 PMID: 23855811
Bouaboula et al (1999) Gi protein modulation induced by a selective inverse agonist for the peripheral cannabinoid receptor CB2: implication for intracellular signalization cross-regulation. Mol.Pharmacol. 55 473 PMID: 10051530
If you know of a relevant reference for SR 144528, please let us know.
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Keywords: SR 144528, SR 144528 supplier, SR144528, high, affinity, selective, cannabinoid, receptors, CB2, inverse, agonists, orally, bioavailable, immunology, Receptors, 5039, Tocris Bioscience
3 Citations for SR 144528
Citations are publications that use Tocris products. Selected citations for SR 144528 include:
Shang et al (2016) Δ 9-Tetrahydrocannabinol Reverses TNFα-induced Increase in Airway Epithelial Cell Permeability through CB 2 Receptors Biochemical Pharmacology PMID: 27641813
Fu (2017) Activation of cannabinoid receptor type 2 by JWH133 alleviates bleomycin-induced pulmonary fibrosis in mice. Oncotarget 8 103486 PMID: 29262578
Presley et al (2015) Preclinical evaluation of SMM-189, a cannabinoid receptor 2-specific inverse agonist. J Neurosci 3 e00159 PMID: 26196013
Do you know of a great paper that uses SR 144528 from Tocris? Please let us know.
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