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A5585

Sigma-Aldrich

5-(N-Methyl-N-isobutyl)­amiloride

≥98% (TLC), powder

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Synonym(s):
MIA
Empirical Formula (Hill Notation):
C11H18ClN7O
CAS Number:
96861-65-3
Molecular Weight:
299.76
MDL number:
MFCD00078567
UNSPSC Code:
12352200
PubChem Substance ID:
24278228
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

form

powder

mp

200-201 °C

solubility

methanol: 9.80-10.20 mg/mL, clear, pale yellow to yellow

storage temp.

2-8°C

SMILES string

CC(C)CN(C)c1nc(N)c(nc1Cl)C(=O)NC(N)=N

InChI

1S/C11H18ClN7O/c1-5(2)4-19(3)9-7(12)16-6(8(13)17-9)10(20)18-11(14)15/h5H,4H2,1-3H3,(H2,13,17)(H4,14,15,18,20)

InChI key

RVIUMPLAOXSSGN-UHFFFAOYSA-N

Gene Information

human ... SCNN1A(6337) , SCNN1B(6338) , SCNN1D(6339) , SCNN1G(6340)
mouse ... Scnn1a(20276) , Scnn1b(20277) , Scnn1d(140501) , Scnn1g(20278)
rat ... Scnn1a(25122) , Scnn1b(24767) , Scnn1g(24768)

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Application

5-(N-Methyl-N-isobutyl)­amiloride is a potent blocker of the Na2/H+ antiport. 5-(N-Methyl-N-isobutyl)­amiloride has been used to study early cellular response to acidosis.

Biochem/physiol Actions

Potent blocker of the Na+/H+ antiport. Possible antitumor agent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The extracellular pH (pHe) in solid tumours is frequently lower than the pHe in normal tissues. Cells within an acidic environment depend on mechanisms which regulate intracellular pH (pHi) for their survival, including the Na+/H+ antiport which exports protons in
X H Xiao et al.
Circulation research, 85(8), 723-730 (1999-10-16)
The role of the Na(+)/H(+) exchanger in ischemia, reperfusion, and preconditioning was investigated in isolated perfused rat hearts. Contractile function, [Na(+)](i), and pH(i) were measured; ischemic damage was assessed by the recovery of developed pressure (DP) on reperfusion. After 30
R M Touyz et al.
Hypertension (Dallas, Tex. : 1979), 34(3), 442-449 (1999-09-18)
This study investigated the role of the Na(+)-H+ exchanger (NHE) on angiotensin II (Ang II)-induced activation of Na(+)-dependent Mg2+ transport in vascular smooth muscle cells (VSMCs) from Wistar-Kyoto rats (WKY; n=20) and spontaneously hypertensive rats (SHR; n=20). Intracellular free concentrations
M Horackova et al.
Cardiovascular research, 47(3), 529-536 (2000-08-30)
This study was designed to investigate the cardioprotective effect of the novel lipophilic iron chelator salicylaldehyde isonicotinoyl hydrazone (SIH) against the oxidative stress exerted by H(2)O(2) through the production of OH radical via the Fenton reaction and to compare them
Eric Londin et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(10), E1106-E1115 (2015-02-26)
Two decades after the discovery of the first animal microRNA (miRNA), the number of miRNAs in animal genomes remains a vexing question. Here, we report findings from analyzing 1,323 short RNA sequencing samples (RNA-seq) from 13 different human tissue types.
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