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Merck

N5501

Sigma-Aldrich

Nω-Nitro-L-arginine

≥98% (TLC)

Sinónimos:

L-NNA, N5-(Nitroamidino)-L-2,5-diaminopentanoic acid, NG-NO2-L-Arg

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About This Item

Fórmula empírica (notación de Hill):
C6H13N5O4
Número de CAS:
Peso molecular:
219.20
Beilstein/REAXYS Number:
1728914
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

assay

≥98% (TLC)

form

powder

mp

257 °C

solubility

1 M HCl: 50 mg/mL, clear, colorless to faintly yellow

SMILES string

N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O

InChI

1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1

InChI key

MRAUNPAHJZDYCK-BYPYZUCNSA-N

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Application

Nω-Nitro-L-arginine has been used:
  • as nitric oxide synthase (NOS) inhibitor, to measure the release of nitric oxide (NO) derivatives in cytochrome c reduction assay
  • to pretreat fiber bundles for contractile studies
  • as NOS inhibitor to characterize the generation of NO in Taxus yunnanensis cells
  • as an irreversible inhibitor of the neuronal NO synthase (nNOS) to preincubate swimbladder preparations

Biochem/physiol Actions

Nω-Nitro-L-arginine/L-NNA helps to reduce the levels of cortical hyperemia and brain cGMP occurring due to hypercapnia.
Irreversible inhibitor of constitutive nitric oxide synthase (nNOS) and a reversible inhibitor of inducible nitric oxide synthase (iNOS).

Features and Benefits

This compound is featured on the Nitric Oxide Synthases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Nitric oxide modulates excitation-contraction coupling in the diaphragm
Reid M B, et al.
Comparative Biochemistry and Physiology. Part A, Molecular & Integrative Physiology, 119(1), 211-218 (1998)
L-NNA decreases cortical hyperemia and brain cGMP levels following CO2 inhalation in Sprague-Dawley rats
Irikura K, et al.
The American Journal of Physiology, 267(2), H837-H843 (1994)
Involvement of nitric oxide in oxidative burst, phenylalanine ammonia-lyase activation and Taxol production induced by low-energy ultrasound in Taxus yunnanensis cell suspension cultures.
Wang JW
Nitric Oxide, 15(4), 351-358 (2006)
Ai-Ling Lin et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 33(9), 1412-1421 (2013-06-27)
Vascular pathology is a major feature of Alzheimer's disease (AD) and other dementias. We recently showed that chronic administration of the target-of-rapamycin (TOR) inhibitor rapamycin, which extends lifespan and delays aging, halts the progression of AD-like disease in transgenic human
Ming-Guo Feng et al.
American journal of physiology. Renal physiology, 303(5), F775-F782 (2012-06-08)
Nebivolol is a β(1)-adrenergic blocker that also elicits renal vasodilation and increases the glomerular filtration rate (GFR). However, its direct actions on the renal microvasculature and vasodilator mechanism have not been established. We used the in vitro blood-perfused juxtamedullary nephron

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