5-(N,N-Hexamethylene)-amiloride

Names

[ Name ]:
5-(N,N-Hexamethylene)-amiloride

[Synonym ]:
HMA
3-amino-5-azepan-1-yl-6-chloro-pyrazine-2-carboxylic acid carbamimidoylamide
HMA-5
3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
Hexamethyleneamiloride

Biological Activity

[Description]:

5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) derives from an amiloride and is a potent Na+/H+ exchanger inhibitor, which decreases the intracellular pH (pHi) and induces apoptosis in leukemic cells. 5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) is also an inhibitor of the HIV-1 Vpu virus ion channel and inhibits mouse hepatitis virus (MHV) replication and human coronavirus 229E (HCoV229E) replication in cultured L929 cells with EC50s of 3.91 μM and 1.34 μM, respectively[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[Target]

Na+/H+ exchanger[1] EC50: 3.91 μM (MHV replication), 1.34 μM (HCoV229E replication)[2]

[References]

[1]. Rich IN, et al. Apoptosis of leukemic cells accompanies reduction in intracellular pH after targeted inhibition of the Na(+)/H(+) exchanger. Blood. 2000 Feb 15;95(4):1427-34.

[2]. Wilson L, et al. Hexamethylene amiloride blocks E protein ion channels and inhibits coronavirus replication. Virology. 2006 Sep 30;353(2):294-306. Epub 2006 Jul 3.

Chemical & Physical Properties

[ Density]:
1.63g/cm3

[ Boiling Point ]:
638.2ºC at 760mmHg

[ Molecular Formula ]:
C₁₂H₁₈ClN₇O

[ Molecular Weight ]:
311.77100

[ Flash Point ]:
339.8ºC

[ Exact Mass ]:
311.12600

[ PSA ]:
136.51000

[ LogP ]:
2.55300

[ Vapour Pressure ]:
3.47E-16mmHg at 25°C

[ Index of Refraction ]:
1.742

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H311-H331

[ Precautionary Statements ]:
P261-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
23/24/25

[ Safety Phrases ]:
22-36/37/39-45

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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