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Merck

N5501

Nω-Nitro-L-arginine

synthetic, ≥98% (TLC), Nitric oxide synthase inhibitor, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H13N5O4
CAS Number:
2149-70-4
Molecular Weight:
219.20
NACRES:
NA.77
PubChem Substance ID:
24278010
UNSPSC Code:
12352209
EC Number:
218-418-9
MDL number:
MFCD00007033
Beilstein/REAXYS Number:
1728914
Assay:
≥98% (TLC)
Form:
powder
Quality level:
200

Key Documents

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Product Name

Nω-Nitro-L-arginine, ≥98% (TLC)

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

SMILES string

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

InChI key

MRAUNPAHJZDYCK-BYPYZUCNSA-N

biological source

synthetic

assay

≥98% (TLC)

form

powder

mp

257 °C

solubility

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

Quality Level

200

Gene Information

human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
mouse ... Nos2(18126)
rat ... Grin2a(24409), Nos1(24598)

Related Categories

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

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

N5501-25G: + N5501-VAR: + N5501-1G: + N5501-5G: + N5501-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH2076
BCCF9639
BCCD9665
1413116V
1413116

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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)
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)
Comp Biochem Physiol A Mol Integr Physiol
Schwerte T, et al.
The Journal of Experimental Biology, 202(8), 1005-1013 (1999)
Tiziana Sinagra et al.
Biochemical pharmacology, 85(4), 551-559 (2012-12-01)
Thiazolidinediones (also referred to as glitazones), agonists for Peroxisome Proliferator-Activated Receptor gamma (PPARγ), are used for treating type 2 diabetes mellitus, where they decrease insulin resistance and cardiovascular risk. Compounds bearing the thiazolidinedione structure have also been shown to inhibit
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