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Merck
CN

SML1814

3,6-DMAD hydrochloride

≥98% (HPLC)

Synonym(s):

N9-(3-(Dimethylamino)propyl)-N3,N3,N6,N6-tetramethylacridine-3,6,9-triamine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H32N5 · xHCl
CAS Number:
2187367-10-6
Molecular Weight:
366.52 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI

1S/C22H31N5/c1-25(2)13-7-12-23-22-18-10-8-16(26(3)4)14-20(18)24-21-15-17(27(5)6)9-11-19(21)22/h8-11,14-15H,7,12-13H2,1-6H3,(H,23,24)

InChI key

UIWOQSJSDYDIQJ-UHFFFAOYSA-N

SMILES string

CN(C)CCCNC1=C2C(C=C(N(C)C)C=C2)=NC3=C1C=CC(N(C)C)=C3

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

yellow to orange

solubility

DMSO: 25 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

3,6-DMAD is also called as N9-(3-(dimethylamino)propyl)-N3,N3,N6,N6-tetramethylacridine-3,6,9-triamine. It prevents the development of multiple myeloma (MM) tumor xenografts.
3,6-DMAD is an acridine derivative that selectively suppresses ER stress- (300 nM Thapsigargin) induced HT1080 cellular XBP1 mRNA splicing (Eff. conc. 500 nM), but not eIF2a phosphorylation, by directly inhibiting IRE1? RNase (endoribonuclease) activity and disrupting IRE1α oligomerization. 3,6-DMAD is shown to exhibit anti-multiple myeloma efficacy in cultures in vitro (%survival/[3,6-DMAD]/cell line/24 h = 13%/4 M/RPMI 8226 and 8%/1 μM/MM1.R) and completely suppress the expansion of established RPMI 8226 tumor in mice in vivo when administered via intraperitoneal injection (10 mg/kg q.o.d.).
3,6-DMAD is an acridine derivative.

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
017M4733V

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Dadi Jiang et al.
Molecular cancer therapeutics, 15(9), 2055-2065 (2016-06-17)
Using a luciferase reporter-based high-throughput chemical library screen and topological data analysis, we identified N-acridine-9-yl-N',N'-dimethylpropane-1,3-diamine (DAPA) as an inhibitor of the inositol requiring kinase 1α (IRE1α)-X-box binding protein-1 (XBP1) pathway of the unfolded protein response. We designed a collection of
Acridine Derivatives as Inhibitors of the IRE1 alpha-XBP1 Pathway Are Cytotoxic to Human Multiple Myeloma
Jiang D, et al.
Molecular Cancer Therapeutics (2016)

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