Hexamethylene bisacetamide Chemical Properties

Melting point:

128-129 °C(lit.)

Boiling point:

338.01°C (rough estimate)

Density 

0.974

refractive index 

1.4710 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

water: soluble5%, clear, colorless

form 

A solid

pka

16.20±0.46(Predicted)

BRN 

1775764

InChI

InChI=1S/C10H20N2O2/c1-9(13)11-7-5-3-4-6-8-12-10(2)14/h3-8H2,1-2H3,(H,11,13)(H,12,14)

InChIKey

BNQSTAOJRULKNX-UHFFFAOYSA-N

SMILES

C(NC(=O)C)CCCCCNC(=O)C

CAS DataBase Reference

3073-59-4(CAS DataBase Reference)

Safety Information

Risk Statements 

33

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

AC2976200

HS Code 

29241990

Toxicity

human,TDLo,intravenous,4270mg/kg/10D (4270mg/kg),GASTROINTESTINAL: NAUSEA OR VOMITINGBLOOD: THROMBOCYTOPENIA,Cancer Research. Vol. 47, Pg. 5788, 1987.

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Hexamethylene bisacetamide Usage And Synthesis

Chemical Properties

white crystalline powder or flakes

Uses

N,N′-Hexamethylene bis(acetamide) was used as an inducing agent in obtaining mononuclear cells from the peripheral blood (PB) sample by Ficoll-Hypaque gradient separation.

Definition

ChEBI: N-(6-acetamidohexyl)acetamide is a member of acetamides.

Biological Activity

Hexamethylene bisacetamide is a tumor cell-differentiating agent. It induces complete differentiation of 754A murine erythroleukemia cells when used at a concentration of 5 mM. Hexamethylene bisacetamide also induces latent HIV-1 viral production in chronically HIV-1-infected U1 cells in a concentration-dependent manner. Implantation of HT-29 colon cancer cells cultured with hexamethylene bisacetamide for seven days, but not 28, reduces tumorigenesis of those cells in mice. Hexamethylene Bisacetamide (HMBA) is a hybrid polar compound originally developed as a differentiation-inducing agent. HMBA can inhibit the activation of several NF kappaB target genes in both lung and breast cancer cell lines. Furthermore, consistent with its ability to inhibit NF kappaB function, HMBA can also sensitize cells to apoptosis. HMBA mediates inhibition of the Akt and ERK/MAPK cascade, both critical for cell survival and proliferation and are well-known regulators of NF kappaB activation[1].

References

[1] Anwesha Dey. “Hexamethylene bisacetamide (HMBA) simultaneously targets AKT and MAPK pathway and represses NF kappaB activity: implications for cancer therapy.” Cell Cycle 7 23 (2008): 3759–67.

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