An amiloride derivative with diverse biological activities
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5-(N,N-hexamethylene)-Amiloride

Item No. 29788

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.2 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $44

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    10 mg

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    25 mg

    $120

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    50 mg

    $215

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    Product Description

    5-(N,N-hexamethylene)-Amiloride (HMA) is a derivative of amiloride (Item No. 14409) with diverse biological activities.1,2,3,4,5 It is an allosteric antagonist of adenosine A2A receptors (Ki = 3.3 µM).2 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.1 It also blocks the cation-selective ion channels formed by the hepatitis C virus (HCV) protein p7.3 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.4 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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ewart, G.D., Mills, K., Cox, G.B., et al. Amiloride derivatives block ion channel activity and enhancement of virus-like particle budding caused by HIV-1 protein Vpu. Eur. Biophys. J. 31(1), 26-35 (2002).

    2. Gao, Z.-G., and Ijzerman, A.P. Allosteric modulation of A2A adenosine receptors by amiloride analogues and sodium ions. Biochem. Pharmacol. 60(5), 669-679 (2000).

    3. Premkumar, A., Wilson, L., Ewart, G.D., et al. Cation-selective ion channels formed by p7 of hepatitis C virus are blocked by hexamethylene amiloride. FEBS Lett. 557(1-3), 99-103 (2004).

    4. Rowson-Hodel, A.R., Berg, A.L., Wald, J.H., et al. Hexamethylene amiloride engages a novel reactive oxygen species- and lysosome-dependent programmed necrotic mechanism to selectively target breast cancer cells. Cancer Lett. 375(1), 62-72 (2016).

    5. Meng, H.-P., Maddaford, T.G., and Pierce, G.N. Effect of amiloride and selected analogues on postischemic recovery of cardiac contractile function. Am. J. Physiol. 264(6 Pt. 2), H1831-H1835 (1993).