A precursor to NOS inhibitor, L-NNA
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L-NAME (hydrochloride)

Item No. 80210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N5-[imino(nitroamino)methyl]-L-ornithine, methyl ester, monohydrochloride
CAS Number
51298-62-5
Synonyms
  • L-NG-Nitroarginine methyl ester
  • N(G)-Nitro-L-arginine methyl ester
Molecular Formula
C7H15N5O4 • HCl
Formula Weight
269.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlEthanol: <50 µg/mlMethanol: 10 mg/mlPBS pH 7.2: 30 mg/ml
SMILES
[H]N(/C(N([H])CCC[C@H](N)C(OC)=O)=N/[H])[N+]([O-])=O.Cl
InChi Code
InChI=1S/C7H15N5O4.ClH/c1-16-6(13)5(8)3-2-4-10-7(9)11-12(14)15;/h5H,2-4,8H2,1H3,(H3,9,10,11);1H
InChi Key
QBNXAGZYLSRPJK-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    Product Description

    L-NAME requires hydrolysis of the methyl ester by cellular esterases to become a fully functional inhibitor (L-NNA).1 L-NNA exhibits some selectivity for inhibition of neuronal and endothelial isoforms. It exhibits Ki values of 15 nM, 39 nM, and 4.4 µM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively.2,3,4 The reported Ki value for the inhibition of iNOS ranges from 4-65 µM.3,5 L-NAME inhibits cGMP formation in endothelial cells with an IC50 of 3.1 µM (in the presence of 30 µM arginine) and reverses the vasodilation effects of acetylcholine in rat aorta rings with an EC50 of 0.54 µM.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Griffith, O.W., and Kilbourn, R.G. Nitric oxide synthase inhibitors: Amino acids. Methods Enzymol. 268, 375-392 (1996).

    2. Buckner, C.K., Saban, R., Castleman, W.L., et al. Analysis of leukotriene receptor antagonists on isolated human intralobar airways. Ann. N. Y. Acad. Sci. 524, 181-186 (1988).

    3. Furfine, E.S., Harmon, M.F., Paith, J.E., et al. Selective inhibition of constitutive nitric oxide synthase by L-NG-nitroarginine. Biochemistry 32, 8512-8517 (1993).

    4. Garvey, E.P., Tuttle, J.V., Covington, K., et al. Purification and characterization of the constitutive nitric oxide synthase from human placenta. Arch. Biochem. Biophys. 311(2), 235-241 (1994).

    5. Abu-Soud, H.M., Feldman, P.L., Clark, P., et al. Electron transfer in the nitric-oxide synthases. Characterization of L-arginine analogs that block heme iron reduction. The Journal of Biological Chemisty 269, 32318-32326 (1994).

    6. Rees, D.D., Palmer, R.M.J., Schulz, R., et al. Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo. Br. J. Pharmacol. 101(3), 746-752 (1990).

    7. Moore, P.K., al-Swayeth, O.A., Chong, N.W.S., et al. L-NG-Nitro arginine (L-NOARG), a novel, L-arginine-reversible inhibitor of endothelium-dependent vasodilatation in vitro. Br. J. Pharmacol. 99, 408-412 (1990).

    Product Citations

    Zhao, X., Guo, Y., Jiang, C., et al. JNK1 negatively controls antifungal innate immunity by suppressing CD23 expression. Nat. Med. 23(3), 337-346 (2017).

    Li, L., Zhu, L., Hao, B., et al. iNOS-derived nitric oxide promotes glycolysis by inducing pyruvate kinase M2 nuclear translocation in ovarian cancer. Oncotarget 8(20), 33047-33063 (2017).

    Jarazo Dietrich, S., Fass, M.I., Jacobo, P.V., et al. Inhibition of NOS-NO system prevents autoimmune orchitis development in rats: Relevance of NO released by testicular macrophages in germ cell apoptosis and testosterone secretion. PLoS One 10(6), e0128709 (2015).

    Premer, C., Blum, A., Bellio, M.A., et al. Allogeneic mesenchymal stem cells restore endothelial function in heart failure by stimulating endothelial progenitor cells. EBioMedicine 2, 467-475 (2015).

    Reese, J., O'Mara, P.W., Poole, S.D., et al. Regulation of the fetal mouse ductus arteriosus is dependent on interaction of nitric oxide and COX enzymes in the ductal wall. Prostaglandins Other Lipid Mediat. 88(3-4), 89-96 (2009).