N5751
Nω-Nitro-L-arginine methyl ester hydrochloride
≥97% (TLC), powder, nitric oxide production inhibitor
Synonym(s):
L-NAME HCl, L-NAME hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C7H15N5O4 · HCl
CAS Number:
Molecular Weight:
269.69
Beilstein:
3744166
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77
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Product Name
Nω-Nitro-L-arginine methyl ester hydrochloride, ≥97% (TLC), powder
biological source
synthetic
Quality Level
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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