ChemicalBook > CAS DataBase List > 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

Product Name
1-(2,3-DICHLOROBENZOYL)-5-METHOXY-2-METHYL-3-[2-(4-MORPHOLINYL)ETHYL]-1H-INDOLE
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-DICHLORO-PHENYL)-[5-METHOXY-2-METHYL-3-(2-MORPHOLIN-4-YL-ETHYL)-INDOL-1-YL]-METHAN;(2,3-Dichlorophenyl)[5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indol-1-yl]methanone;(2,3-DICHLORO-PHENYL)-[5-METHOXY-2-METHYL-3-(2-MORPHOLIN-4-YL-ETHYL)-INDOL-1-YL]-METHANONE;Methanone,(2,3-dichlorophenyl)[5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indol-1-yl]-
CBNumber
CB1148019
Molecular Formula
C23H24Cl2N2O3
Formula Weight
447.35
MOL File
180002-83-9.mol
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1-(2,3-DICHLOROBENZOYL)-5-METHOXY-2-METHYL-3-[2-(4-MORPHOLINYL)ETHYL]-1H-INDOLE Property

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
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Safety

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
HazardClass 
6.1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
G1421
Product name
GW405833 hydrochloride
Purity
≥98% (HPLC), solid
Packaging
5mg
Price
$133
Updated
2025/07/31
Sigma-Aldrich
Product number
G1421
Product name
GW405833 hydrochloride
Purity
≥98% (HPLC), solid
Packaging
25mg
Price
$570
Updated
2025/07/31
TCI Chemical
Product number
G0600
Product name
GW-405833
Packaging
10MG
Price
$125
Updated
2025/07/31
Cayman Chemical
Product number
20219
Product name
GW 405833
Purity
≥98%
Packaging
1mg
Price
$34
Updated
2024/03/01
Cayman Chemical
Product number
20219
Product name
GW 405833
Purity
≥98%
Packaging
5mg
Price
$85
Updated
2024/03/01
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1-(2,3-DICHLOROBENZOYL)-5-METHOXY-2-METHYL-3-[2-(4-MORPHOLINYL)ETHYL]-1H-INDOLE Chemical Properties,Usage,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

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1-(2,3-DICHLOROBENZOYL)-5-METHOXY-2-METHYL-3-[2-(4-MORPHOLINYL)ETHYL]-1H-INDOLE Suppliers

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180002-83-9, 1-(2,3-DICHLOROBENZOYL)-5-METHOXY-2-METHYL-3-[2-(4-MORPHOLINYL)ETHYL]-1H-INDOLERelated Search:

1-(2,3-DICHLOROBENZOYL)-5-METHOXY-2-METHYL-3-[2-(4-MORPHOLINYL)ETHYL]-1H-INDOLE (3-(2-AMINOETHYL)-1-METHYLINDOLE) 2HCL N-ACETYL-6-METHOXYTRYPTAMINE N-ACETYL-5-HYDROXYTRYPTAMINE CHEMBRDG-BB 5102396 Benanserine

  • GW 405833
  • (2,3-DICHLORO-PHENYL)-[5-METHOXY-2-METHYL-3-(2-MORPHOLIN-4-YL-ETHYL)-INDOL-1-YL]-METHANONE
  • 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]-METHAN
  • 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-(3-(morpholin-4-yl)ethyl)-1H-indole hydrochloride
  • GW405833 hydrochloride
  • (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]-
  • (2,3-dichlorophenyl)-[5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1-indolyl]methanone hydrochloride
  • L-768242
  • (2,3-Dichlorophenyl)[5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indol-1-yl]methanone
  • GW405833,GW 405833,Cannabinoid Receptor,GW-405833,L768242,anti-inflammatory,Inhibitor,L 768242,neuropathic pain,inhibit
  • GW 405833, 10 mM in DMSO
  • 180002-83-9
  • C23H24Cl2N2O3HCl
  • C23H24Cl2N2O3