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L-NAME (hydrochloride)

Item № 80210
CAS № 51298-62-5
Purity ≥99%
product image
                (CAS 51298-62-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 g $13.00 0.00
     5 g $59.00 0.00
     10 g $98.00 0.00
     50 g $423.00 0.00

Pricing updated 2019-05-23. Prices are subject to change without notice.

Description
Synonyms
  • L-NG-Nitroarginine methyl ester
  • N(G)-Nitro-L-arginine methyl ester

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

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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
≥99%
Formulation
A crystalline solid
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

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 1 year
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Additional Information

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References & Product Citations
Product Description References

1. Griffith, O.W., and Kilbourn, R.G. Nitric oxide synthase inhibitors: Amino acids Methods in Enzymology 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 Annals of the New York Academy of Sciences 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 Archives of Biochemistry and Biophysics 311, 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 British Journal of Pharmacology 101, 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 British Journal of Pharmacology 99, 408-412 (1990).

Product Citations

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).

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