ChemicalBook CAS DataBase List 1154-25-2

1154-25-2

Name	EIPA
CAS	1154-25-2
Molecular Formula	C11H18ClN7O
MDL Number	MFCD00151710
Molecular Weight	299.76
MOL File	1154-25-2.mol

Synonyms

EIPA L 593754 MH 12-43 ethylisopropylamiloride 5-(N-ETHYL-N-ISOPROPYL)AMILORIDE AMILORIDE, 5-(N-ETHYL-N-ISOPROPYL)- 3-AMino-N-(aMinoiMinoMethyl)-6-chloro-5-[ethyl(1-Methylethyl)aMino]- 3-amino-6-chloro-N-(diaminomethylene)-5-[ethyl(isopropyl)amino]pyrazinamide 3-aMino-N-carbaMiMidoyl-6-chloro-5-(ethyl(isopropyl)aMino)pyrazine-2-carboxaMide 3-AMINO-N-(AMINOIMINOMETHYL)-6-CHLORO-5-[ETHYL(2-PROPYL)AMINO]-PYRAZINE-2-CARBOXAMIDE 3-Amino-5-[ethyl(isopropyl)amino]-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide 6-Chloro-3-amino-5-[ethyl(isopropyl)amino]-N-(diaminomethylene)-2-pyrazinecarboxamide 3-Amino-5-(N-ethyl-N-isopropylamino)-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide 3-Amino-N-(aminoiminomethyl)-6-chloro-5-[ethyl(1-methylethyl)amino]-2-pyrazinecarboxamide 3-amino-6-chloro-N-(diaminomethylidene)-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide 3-azanyl-N-[bis(azanyl)methylidene]-6-chloro-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide

Chemical Properties

Appearance	Yellow Solid
Melting point	202-205 °C(lit.)
density	1.49±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Acetonitrile (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
form	Off-white to yellow solid.
pka	8.67±0.46(Predicted)
color	Pale Yellow to Green
biological source	synthetic
Stability:	Unstable in methanol
InChI	InChI=1S/C11H18ClN7O/c1-4-19(5(2)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)
InChIKey	QDERNBXNXJCIQK-UHFFFAOYSA-N
SMILES	C1(C(NC(N)=N)=O)=NC(Cl)=C(N(CC)C(C)C)N=C1N
CAS DataBase Reference	1154-25-2

Safety Data

Hazard Codes	Xi
Risk Statements	36/37/38 less more
Safety Statements	26-37/39 less more
RIDADR	2811
WGK Germany	3
HazardClass	6.1(b)
PackingGroup	III

Hazard Information

Chemical Properties

Yellow Solid

Uses

Selective Na+/H+ antiporter inhibitor. Selectively enhances the excretion of sodium ions without causing an increase in excretion of potassium ions

Description

Sodium-hydrogen exchangers (NHE) are involved in maintaining sodium and pH balance in a variety of tissues. They are also known as sodium-hydrogen antiporters and solute carrier family 9 members. 5-(N-ethyl-N-isopropyl)-Amiloride (EIPA) is a potent inhibitor of several NHE isoforms, inhibiting NHE1, NHE2, NHE3, and NHE5 with K_i values of 0.02, 0.5, 2.4, and 0.42 μM, respectively. It less effectively inhibits NHE4 (IC₅₀ ≥10 μM). EIPA is commonly used at a concentration of 5-10 μM to inhibit cellular HNE activity.

Definition

ChEBI: Ethylisopropylamiloride is a member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group. It has a role as an anti-arrhythmia drug, a neuroprotective agent and a sodium channel blocker. It is a member of guanidines, an aromatic amine, an organochlorine compound, a tertiary amino compound, a member of pyrazines and a monocarboxylic acid amide. It is functionally related to an amiloride.

Biochem/physiol Actions

Selective blocker of Na+/H+ antiport

storage

Store at -20°C

References

[1] B. MASEREEL D. L L Pochet. An overview of inhibitors of Na+/H+ exchanger[J]. European Journal of Medicinal Chemistry, 2003, 38 6: Pages 547-554. DOI: 10.1016/s0223-5234(03)00100-4
[2] S ATTAPHITAYA J E M K Park. Molecular cloning and functional expression of a rat Na+/H+ exchanger (NHE5) highly expressed in brain.[J]. The Journal of Biological Chemistry, 1999, 274 7: 4383-4388. DOI: 10.1074/jbc.274.7.4383
[3] SUNG-MIN HWANG. Intracellular acidification is associated with changes in free cytosolic calcium and inhibition of action potentials in rat trigeminal ganglion.[J]. The Journal of Biological Chemistry, 2011: 1719-1729. DOI: 10.1074/jbc.m109.090951
[4] LIN XUE. Trefoil factor 2 requires Na/H exchanger 2 activity to enhance mouse gastric epithelial repair.[J]. The Journal of Biological Chemistry, 2011: 38375-38382. DOI: 10.1074/jbc.m111.268219

Spectrum Detail

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