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G1421

Sigma-Aldrich

GW405833 hydrochloride

≥98% (HPLC), solid

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Synonym(s):
1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-(3-(morpholin-4-yl)ethyl)-1H-indole hydrochloride, 242 hydrochloride, L-768, L-768242 hydrochloride, L768242 hydrochloride, ML-SI1 hydrochloride
Empirical Formula (Hill Notation):
C23H24Cl2N2O3 · HCl
CAS Number:
Molecular Weight:
483.82
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

color

white to pink

solubility

DMSO: soluble >10 mg/mL
H2O: insoluble <2 mg/mL

storage temp.

2-8°C

SMILES string

Cl.COc1ccc2n(c(C)c(CCN3CCOCC3)c2c1)C(=O)c4cccc(Cl)c4Cl

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

InChI key

JIQYDHDVNNFPMU-UHFFFAOYSA-N

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This Item
D101SML1386SML0190
GW405833 hydrochloride &#8805;98% (HPLC), solid

Sigma-Aldrich

G1421

GW405833 hydrochloride

(±)-DOI hydrochloride &#8805;98% (HPLC), solid

Sigma-Aldrich

D101

(±)-DOI hydrochloride

ML133 hydrochloride &#8805;95% (HPLC)

Sigma-Aldrich

SML0190

ML133 hydrochloride

form

solid

form

solid

form

powder

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

drug control

-

drug control

-

drug control

-

storage condition

desiccated

storage condition

-

storage condition

-

storage condition

desiccated

color

white to pink

color

white to off-white

color

white to beige

color

white to tan

solubility

DMSO: soluble >10 mg/mL, H2O: insoluble <2 mg/mL

solubility

H2O: 10 mg/mL, ethanol: 2 mg/mL

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: ≥10 mg/mL

Application

GW405833 hydrochloride has been used as a lysosomal transient receptor potential mucolipin 1 (TRPML1) specific inhibitor to validate if TRPML1 mediates tau release in neurons and also to verify if it mediates the release of lysosomal tau. It has also been used as a TRPML channel blocker to study the effect of mucolipin transient receptor potential cation channel 3 (MCOLN3/TRPML3) function and trafficking on autophagy in HeLa cells.

Biochem/physiol Actions

GW405833 hydrochloride, also known as ML-SI1, is a cell-permeable lysosomal transient receptor potential cation channel, mucolipin subfamily (TRPML) blocker.
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.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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I Dando et al.
Cell death & disease, 4, e664-e664 (2013-06-15)
The anti-tumoral effects of cannabinoids have been described in different tumor systems, including pancreatic adenocarcinoma, but their mechanism of action remains unclear. We used cannabinoids specific for the CB1 (ACPA) and CB2 (GW) receptors and metabolomic analyses to unravel the
M Donadelli et al.
Cell death & disease, 2, e152-e152 (2011-04-29)
Gemcitabine (GEM, 2',2'-difluorodeoxycytidine) is currently used in advanced pancreatic adenocarcinoma, with a response rate of < 20%. The purpose of our work was to improve GEM activity by addition of cannabinoids. Here, we show that GEM induces both cannabinoid receptor-1
Charlotte Leser et al.
European journal of medicinal chemistry, 210, 112966-112966 (2020-11-15)
The members of the TRPML subfamily of non-selective cation channels (TRPML1-3) are involved in the regulation of important lysosomal and endosomal functions, and mutations in TRPML1 are associated with the neurodegenerative lysosomal storage disorder mucolipidosis type IV. For in-depth investigation
Bethan S Kilpatrick et al.
Journal of cell science, 129(20), 3859-3867 (2016-09-01)
Transient receptor potential (TRP) mucolipins (TRPMLs), encoded by the MCOLN genes, are patho-physiologically relevant endo-lysosomal ion channels crucial for membrane trafficking. Several lines of evidence suggest that TRPMLs mediate localised Ca2+ release but their role in Ca2+ signalling is not
Yin Xu et al.
Molecular psychiatry, 26(10), 5925-5939 (2020-05-06)
Neurofibrillary tangles (NFTs) composed of hyperphosphorylated and misfolded tau protein are a pathological hallmark of Alzheimer's disease and other tauopathy conditions. Tau is predominantly an intraneuronal protein but is also secreted in physiological and pathological conditions. The extracellular tau has

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