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N5751

Sigma-Aldrich

Nω-Nitro-L-arginine methyl ester hydrochloride

≥97% (TLC), powder

Synonym(s):

L-NAME HCl, L-NAME hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C7H15N5O4 · HCl
CAS Number:
51298-62-5
Molecular Weight:
269.69
Beilstein/REAXYS Number:
3744166
EC Number:
257-116-1
MDL number:
MFCD00039052
UNSPSC Code:
12352209
PubChem Substance ID:
24278011
NACRES:
NA.77

biological source

synthetic

Quality Level

200

assay

≥97% (TLC)

form

powder

color

white to off-white

mp

132 °C

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

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

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/t5-;/m0./s1

InChI key

QBNXAGZYLSRPJK-JEDNCBNOSA-N

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General description

Nω-Nitro-L-argininemethyl ester hydrochloride or L -NAME HCl, ananalog of arginine, inhibits NO production. It has multiple effects on thevascular system. Inhibits relaxation induced by acetylcholine and induces anincrease in arterial blood pressure. Abolishes lecithinized superoxidedismutase induced vasodilation when used to pretreat aortic ring preparationsof mice. Induces leukocyte adhesion and increases microvascular fluid andprotein fluxes and permeability. It has also been used in many studies oflearning and memory.

Application

Nω-Nitro-L-arginine methyl ester hydrochloride has been used:
  • to study the effects of brain-derived neurotrophic factor against neurotoxicity in rat cortical neurons
  • to study its effect on far-infrared (FIR) enhanced microcirculation of rat skin
  • to study its effect on leptin-induced regulation of myokine fibronectin type III domain containing five/irisin in murine myocytes and fat cells
  • to study its effect on the levels of arginine vasopressin and neuronal nitric oxide synthase mRNA levels in hypothalamic paraventricular nucleus and supraoptic nucleus of rat

Biochem/physiol Actions

Arginine analog that inhibits NO production.

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nitric Oxide Synthase, Neuronal Inhibitor I The Nitric Oxide Synthase, Neuronal Inhibitor I, also referenced under CAS 357965-99-2, controls the biological activity of neuronal Nitric Oxide Synthase. This small molecule/inhibitor is primarily used for Inflammation/Immunology applications.

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L B Zou et al.
Neuropharmacology, 37(3), 323-330 (1998-07-29)
We investigated the role of nitric oxide (NO) in learning and memory formation in a radial maze test, by using the NO synthase (NOS) inhibitors, NG-nitro-L-arginine methyl ester (L-NAME) and 7-nitroindazole (7-NI), and an NO precursor, L-arginine. Rats were trained
P Kubes et al.
The American journal of physiology, 262(2 Pt 2), H611-H615 (1992-02-01)
We recently demonstrated that inhibitors of nitric oxide (NO) production cause a dramatic increase in leukocyte adherence and emigration in postcapillary venules. The objective of this study was to assess whether inhibition of NO production leads to vascular protein leakage
Lisa Nguy et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 304(9), R744-R752 (2013-03-22)
Rats with adenine-induced chronic renal failure (A-CRF) develop metabolic and cardiovascular abnormalities resembling those in patients with chronic kidney disease. The aim of this study was to investigate the mechanisms of hypertension in this model and to assess aortic stiffness
Protective effects of brain-derived neurotrophic factor against neurotoxicity of 3-nitropropionic acid in rat cortical neurons.
Wu CL, et al.
Neurotoxicology, 30(4), 718-726 (2009)
Amanda E Boe et al.
Circulation, 128(21), 2318-2324 (2013-10-05)
Long-term inhibition of nitric oxide synthase by L-arginine analogues such as N(ω)-nitro-l-arginine methyl ester (L-NAME) has been shown to induce senescence in vitro and systemic hypertension and arteriosclerosis in vivo. We previously reported that plasminogen activator inhibitor-1 (PAI-1)-deficient mice (PAI-1(-/-))
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