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N5501

Sigma-Aldrich

Nω-Nitro-L-arginine

≥98% (TLC)

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Synonym(s):
L-NNA, N5-(Nitroamidino)-L-2,5-diaminopentanoic acid, NG-NO2-L-Arg
Empirical Formula (Hill Notation):
C6H13N5O4
CAS Number:
Molecular Weight:
219.20
Beilstein/REAXYS Number:
1728914
EC Number:
MDL number:
PubChem Substance ID:

biological source

synthetic

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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1 of 4

This Item
N5751M7033A3133
vibrant-m

N5501

Nω-Nitro-L-arginine

vibrant-m

M7033

NG-Methyl-L-arginine acetate salt

vibrant-m

A3133

Nα-Acetyl-L-arginine

form

powder

form

powder

form

powder

form

powder

assay

≥98% (TLC)

assay

≥97% (TLC)

assay

≥98% (TLC)

assay

≥98% (TLC)

solubility

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

solubility

H2O: 50 mg/mL

solubility

water: 49.00-51.00 mg/mL, clear to very slightly hazy, colorless to faintly yellow

solubility

-

biological source

synthetic

biological source

synthetic

biological source

-

biological source

-

mp

257 °C

mp

132 °C

mp

-

mp

-

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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Nα-Acetyl-L-arginine

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)
Cyclic GMP is a second messenger by which nitric oxide inhibits diaphragm contraction
Abraham R Z, et al.
Comparative Biochemistry and Physiology. Part A, Molecular & Integrative Physiology, 119(1), 177-183 (1998)
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)
Mark W Gorman et al.
American journal of physiology. Heart and circulatory physiology, 299(6), H1981-H1989 (2010-09-21)
The adenine nucleotide hypothesis postulates that the ATP released from red blood cells is broken down to ADP and AMP in coronary capillaries and that ATP, ADP, and AMP act on purinergic receptors on the surface of capillary endothelial cells.

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