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Merck

SML0952

NSC23766 trihydrochloride

≥97% (HPLC), Rac1 inhibitor, powder

Synonym(s):

N6-[2-(4-Diethylamino-1-methyl-butylamino)-6-methyl-pyrimidin-4-yl]-2-methyl-quinoline-4,6-diamine trihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C24H35N7 · 3HCl
CAS Number:
1177865-17-6
Molecular Weight:
530.96
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

NSC23766 trihydrochloride, ≥97% (HPLC)

SMILES string

Cl.Cl.Cl.N(CCCC(Nc1nc(cc(n1)C)Nc2cc3c(nc(cc3N)C)cc2)C)(CC)CC

InChI

1S/C24H35N7.3ClH/c1-6-31(7-2)12-8-9-16(3)27-24-28-18(5)14-23(30-24)29-19-10-11-22-20(15-19)21(25)13-17(4)26-22;;;/h10-11,13-16H,6-9,12H2,1-5H3,(H2,25,26)(H2,27,28,29,30);3*1H

InChI key

CPUHORIUXPQCHW-UHFFFAOYSA-N

assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Application

NSC23766 trihydrochloride has been used as a ras-related C3 botulinum toxin substrate 1 (RAC1) inhibitor.

Biochem/physiol Actions

NSC23766 is an inhibitor of Rac1, a Rho-family GTPase.
NSC23766 is an inhibitor of Rac1, a Rho-family GTPase. The compound blocks activation by the guanine nucleotide exchange factors Trio and Tiam1, but does not affect interactions with RhoA or Cdc42. NSC23766 blocks ADP-mediated platelet aggregation. Inhibition of Rac1 by NSC23766 restores sensitivity to trastuzumab by restoring down-regulation of ErbB2.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000139285
0000139285
0000486166
0000486166
0000456063

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Elaine Vermaak et al.
Virology, 497, 217-232 (2016-08-09)
Cellular pathways involved in cell entry by African horse sickness virus (AHSV), a member of the Orbivirus genus within the Reoviridae family, have not yet been determined. Here, we show that acidic pH is required for productive infection of BSR
Ruifeng Lu et al.
Scientific reports, 6, 38249-38249 (2016-12-03)
The generation of cell polarity is essential for the development of multi-cellular organisms as well as for the function of epithelial organs in the mature animal. Small GTPases regulate the establishment and maintenance of polarity through effects on cytoskeleton, membrane
Takumi Kawaue et al.
Developmental cell, 58(4), 267-277 (2023-02-22)
The number of cells in tissues is controlled by cell division and cell death, and its misregulation could lead to pathological conditions such as cancer. To maintain the cell numbers, a cell-elimination process called apoptosis also stimulates the proliferation of
1α, 25 (OH) 2D3 Induces Actin Depolymerization in Endometrial Carcinoma Cells by Targeting RAC1 and PAK1.
Zeng N, et al.
Cellular Physiology and Biochemistry, 40(6), 1455-1464 (2016)
Zhigang Li et al.
Journal of immunology (Baltimore, Md. : 1950), 199(9), 3176-3186 (2017-09-28)
In elderly patients, bacterial infection often causes severe complications and sepsis. Compared to younger patients, older patients are more susceptible to sepsis caused by respiratory infection. Macrophage (Mϕ) phagocytosis of bacteria plays a critical role in the clearance of pathogens
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