M7033

N^G-Methyl-L-arginine acetate salt

Name: N<SUP>G</SUP>-Methyl-<SC>L</SC>-arginine acetate salt
Brand: SIGMA
Price: 71.3 EUR

≥98% (TLC), powder, nitric oxide synthase inhibitor

Synonym(s):

N_ω-Methyl-L-arginine acetate salt, L-NMMA, N⁵-(Methylamidino)-L-ornithine acetate salt, N^G-Monomethyl-L-arginine acetate salt

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€ 121,00

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€ 367,00

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About This Item

Empirical Formula (Hill Notation):

C₇H₁₆N₄O₂ · C₂H₄O₂

CAS Number:

53308-83-1

Molecular Weight:

248.28

NACRES:

NA.77

PubChem Substance ID:

24278043

UNSPSC Code:

12352209

MDL number:

MFCD00069311

Beilstein/REAXYS Number:

6674255

Key Documents

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Product Name

N^G-Methyl-L-arginine acetate salt, ≥98% (TLC)

InChI key

IKPNWIGTWUZCKM-JEDNCBNOSA-N

SMILES string

CC(O)=O.CNC(=N)NCCC[C@H](N)C(O)=O

InChI

1S/C7H16N4O2.C2H4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13;1-2(3)4/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);1H3,(H,3,4)/t5-;/m0./s1

assay

≥98% (TLC)

form

powder

solubility

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

Quality Level

200

Gene Information

human ... NOS1(4842), NOS2(4843), NOS3(4846)
mouse ... Nos2(18126)
rat ... Nos1(24598), Nos2(24599)

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Show Differences

1 of 4

This Item	H7278	N5501	SML1461
Sigma-Aldrich M7033 N^G-Methyl-L-arginine acetate salt	Sigma-Aldrich H7278 N^G-Hydroxy-L-arginine acetate salt	Sigma-Aldrich N5501 N_ω-Nitro-L-arginine	Sigma-Aldrich SML1461 Kyotorphin acetate salt
form powder	form powder	form powder	form powder
assay ≥98% (TLC)	assay ≥98% (TLC)	assay ≥98% (TLC)	assay ≥98% (HPLC)
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 100
solubility water: 49.00-51.00 mg/mL, clear to very slightly hazy, colorless to faintly yellow	solubility acetic acid: 10 mg/mL, clear, colorless to faintly yellow	solubility 1 M HCl: 50 mg/mL, clear, colorless to faintly yellow	solubility H₂O: 20 mg/mL, clear
Gene Information human ... NOS1(4842), NOS2(4843), NOS3(4846) mouse ... Nos2(18126) rat ... Nos1(24598), Nos2(24599)	Gene Information -	Gene Information human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846) mouse ... Nos2(18126) rat ... Grin2a(24409), Nos1(24598)	Gene Information -

Application

N^G-Methyl-L-arginine acetate salt has been used:

as an inhibitor of nitric oxide synthase (NOS) in wound healing studies in injured mice[1]
as an inhibitor of nitric oxide synthase (NOS) to study nitric oxide (NO) immunosuppressive effect of murine stem cells[2]
as an inhibitor to monitor NO levels in hemocytes respiratory burst assay[3]

Biochem/physiol Actions

N^G-Methyl-L-arginine is an inhibitor of nitric oxide synthase in neurons, endothelial cells, and macrophages.[4] It inhibits endothelium-derived relaxing factor and promotes contraction in pulmonary artery and vein. It stereo selectively inhibits the generation of nitric oxide (NO) from arginine.[5] It promotes epinephrine and glucose levels, contributing to hyperglycemia in central nervous system.[6]

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)

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Nitric oxide induces epidermal stem cell de-adhesion by targeting integrin beta1 and Talin via the cGMP signalling pathway

Zhan R, et al.

Nitric Oxide, 78, 1-10 (2018)

NG-methyl-L-arginine, an inhibitor of nitric oxide synthase, affects the central nervous system to produce peripheral hyperglycemia in conscious rats

Uemura K, et al.

Neuroendocrinology, 66(2), 136-144 (1997)

Immune parameters in the common octopus (Octopus vulgaris Cuvier, 1797) naturally infected by the gastrointestinal protozoan parasite Aggregata octopiana

Castellanos-Martinez S and Gestal C

Aquaculture (Amsterdam, Netherlands), 497, 487-493 (2018)

NG-methyl-L-arginine functions as an alternate substrate and mechanism-based inhibitor of nitric oxide synthase

Olken NM and Marletta MA

Biochemistry, 32(37), 9677-9685 (1993)

Reduced susceptibility of clinical strains of Mycobacterium tuberculosis to reactive nitrogen species promotes survival in activated macrophages.

Jonna Idh et al.

PloS one, 12(7), e0181221-e0181221 (2017-07-14)

Drugs such as isoniazid (INH) and pretomanid (PRT), used against Mycobacterium tuberculosis are active partly through generation of reactive nitrogen species (RNS). The aim of this study was to explore variability in intracellular susceptibility to nitric oxide (NO) in clinical

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N^G-Methyl-L-arginine acetate salt