1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
![1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole Structure](CAS/GIF/180002-83-9.gif)
- CAS No.
- 180002-83-9
- Chemical Name:
- 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole
- Synonyms
- L-768242;GW 405833;GW405833 hydrochloride;GW 405833, 10 mM in DMSO;1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole;(2,3-Dichloro-phenyl)-[5-Methoxy-2-Methyl-3-(2-Morpholin-4-yl-ethyl)-indol-1-yl];(2,3-dichlorophenyl)(5-methoxy-2-methyl-3-(2-morpholinoethyl)-1H-indol-1-yl)methanone;(2,3-DICHLORO-PHENYL)-[5-METHOXY-2-METHYL-3-(2-MORPHOLIN-4-YL-ETHYL)-INDOL-1-YL]-METHAN;(2,3-DICHLORO-PHENYL)-[5-METHOXY-2-METHYL-3-(2-MORPHOLIN-4-YL-ETHYL)-INDOL-1-YL]-METHANONE;(2,3-Dichlorophenyl)[5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indol-1-yl]methanone
- CBNumber:
- CB1148019
- Molecular Formula:
- C23H24Cl2N2O3
- Molecular Weight:
- 447.35
- MDL Number:
- MFCD08061200
- MOL File:
- 180002-83-9.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 47-49℃ |
|---|---|
| storage temp. | 2-8°C |
| solubility | Soluble in DMSO at 10-15mg/ml. Also soluble in ethanol at ~5mg/ml. |
| form | solid |
| color | tan |
| InChI | 1S/C23H24Cl2N2O3.ClH/c1-15-17(8-9-26-10-12-30-13-11-26)19-14-16(29-2)6-7-21(19)27(15)23(28)18-4-3-5-20(24)22(18)25;/h3-7,14H,8-13H2,1-2H3;1H |
| InChIKey | JIQYDHDVNNFPMU-UHFFFAOYSA-N |
| SMILES | Cl.COc1ccc2n(c(C)c(CCN3CCOCC3)c2c1)C(=O)c4cccc(Cl)c4Cl |
| FDA UNII | 85K154W99L |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301-H413 | |||||||||
| Precautionary statements | P273-P301+P310+P330 | |||||||||
| PPE | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 25 | |||||||||
| Safety Statements | 45 | |||||||||
| RIDADR | UN 2811 6.1/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| HazardClass | 6.1 | |||||||||
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
|||||||||
| Hazard Classifications | Acute Tox. 3 Oral Aquatic Chronic 4 |
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| NFPA 704 |
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1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole price More Price(39)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | G1421 | GW405833 hydrochloride ≥98% (HPLC), solid | 180002-83-9 | 5mg | $143 | 2026-04-30 | Buy |
| Sigma-Aldrich | G1421 | GW405833 hydrochloride ≥98% (HPLC), solid | 180002-83-9 | 25mg | $611 | 2026-04-30 | Buy |
| TCI Chemical | G0600 | GW-405833 | 180002-83-9 | 10MG | $125 | 2026-04-30 | Buy |
| Cayman Chemical | 20219 | GW 405833 ≥98% | 180002-83-9 | 1mg | $38 | 2026-04-30 | Buy |
| Cayman Chemical | 20219 | GW 405833 ≥98% | 180002-83-9 | 5mg | $94 | 2026-04-30 | Buy |
1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole Chemical Properties, Uses, Production
Uses
It is a potent and selective CB2 receptor partial agonist (EC50 = 0.65 nM; maximum inhibition = 44.6%). Binds with high affinity to both human and rat CB2 receptors and displays ~ 1200-fold selectivity over CB1 (Ki values are 3.92 and 4772 nM for human recombinant CB2 and CB1 receptors respectively). Produces potent antihyperalgesic effects in several rodent models of pain.
Definition
ChEBI: (2,3-dichlorophenyl)-[5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1-indolyl]methanone is a N-acylindole.
Biological Activity
Potent and selective CB 2 receptor partial agonist (EC 50 = 0.65 nM; maximum inhibition = 44.6%). Binds with high affinity to both human and rat CB 2 receptors and displays ~ 1200-fold selectivity over CB 1 (K i values are 3.92 and 4772 nM for human recombinant CB 2 and CB 1 receptors respectively). Produces potent antihyperalgesic effects in several rodent models of pain.
Biochem/physiol Actions
GW405833 is a selective cannabanoid CB2 receptor agonist; analgesic. GW405833 binds with high affinity at both human and rat CB2 receptors (Ki′s 3.9 and 3.6 nM); acts as a partial agonist (50% inhibition of forskolin-stimulated cAMP formation compared to full agonist CP55,940). GW405833 has potent analgesic activity in rat models of inflammatory, neuropathic and incisional pain; devoid of CNS effects common with CB1 agonists.
in vivo
GW-405833 (3, 10 and 30 mg/kg; i.p.) reverses hyperalgesia in both pain models in a dose-dependent manner in WT mice, while this effect is preserves in CB1KO mice but absent in CB2KO mice[1]. GW-405833 (30 mg/kg; i.p.) does not induce cataplexy, motor ataxia, hypothermia, or acute tail-flick antiesthesia in CD1KO mice[1].
| Animal Model: | CB1KO mice, CB2KO mice, WT mice[1] |
| Dosage: | 3, 10 and 30 mg/kg |
| Administration: | Intraperitoneal injection (i.p.) |
| Result: | Increased the paw withdrawal threshold in CB2KO and WT mice in a dose-dependent manner. Restored mechanical paw withdrawal thresholds relative to baseline in CB2KO and WT mice at doses as low as 10 mg/kg. Retained antiallodynic effects in CB2KO mice. Produced a dose-dependent increase in mechanical threshold in WT mice, but this antiallodynic effect was absent in CB1KO mice. Blocked the antihyperalgesic effect by the CB1 antagonist rimonabant (HY-14136), but not by the CB2 antagonist SR144528 (HY-13439). |
IC 50
CB2: 50.7 nM (EC50); CB1: 16.1 μM (EC50)
1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole Preparation Products And Raw materials
Raw materials
Preparation Products
1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Wuhan Chemwish Technology Co., Ltd | 86-027-67849912 | sales@chemwish.com | China | 35884 | 56 |
| Nanjing Chemlin Chemical Co., Ltd | 025-83697070 13770331960 | info@chemlin.com.cn | China | 16305 | 64 |
| BOC Sciences | 1-631-485-4226; 16314854226 | info@bocsci.com | United States | 9920 | 65 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| Shanghai Synchem Pharma Co., ltd | 21-619849051-1 18521059765 | synchempharma@aliyun.com | China | 4988 | 55 |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8435 | 60 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9799 | 58 |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131885 | 58 |
