5-(N,N-hexamethylene)-Amiloride

5-(N,N-hexamethylene)-Amiloride (HMA) is a derivative of amiloride (Cay-14409) with diverse biological activities. It is an allosteric antagonist of adenosine A2A receptors (Ki = 3.3 µM). HMA inhibits the cation-selective ion channel formed by the HIV-1 viral protein Vpu when used at a concentration of 50 µM, as well as budding of virus-like particles in HeLa cells expressing the HIV-1 proteins Gag and Vpu when used at a concentration of 10 µM. It also blocks the cation-selective ion channels formed by the hepatitis C virus (HCV) protein p7. HMA (40 µM) induces necrosis in and reduces the viability of MCF-7, MDA-MB-231, T47D, SK-BR-3, Met-1, and NDL breast cancer cells but not cardiomyocytes or uterine, pulmonary, and renal epithelial cells. HMA protects against post-ischemic contractile dysfunction and reduces coronary effluent creatine phosphokinase activity in a model of ischemia-reperfusion injury using isolated rat right ventricular free walls.Formal Name: 3-amino-N-(aminoiminomethyl)-6-chloro-5-(hexahydro-1H-azepin-1-yl)-2-pyrazinecarboxamide. CAS Number: 1428-95-1. Synonyms: HMA. Molecular Formula: C12H18ClN7O. Formula Weight: 311.8. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 3mg/mL, DMSO: 10mg/mL, DMSO:PBS (pH 7.2) (1:4): 0.2mg/mL. lambdamax: 232, 295, 375 nm. SMILES: ClC1=C(N2CCCCCC2)N=C(N)C(C(NC(N)=N)=O)=N1. InChi Code: InChI=1S/C12H18ClN7O/c13-8-10(20-5-3-1-2-4-6-20)18-9(14)7(17-8)11(21)19-12(15)16/h1-6H2,(H2,14,18)(H4,15,16,19,21). InChi Key: RQQJJXVETXFINY-UHFFFAOYSA-N.