N'-Nitro-L-arginine-methyl ester hydrochloride CAS#: 51298-62-5

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N'-Nitro-L-arginine-methyl ester hydrochloride

Basic information Safety Supplier Related

N'-Nitro-L-arginine-methyl ester hydrochloride Basic information

Product Name:

N'-Nitro-L-arginine-methyl ester hydrochloride

Synonyms:

L-NG-Nitroarginine Methyl Ester (L-NAME)
Nω-Nitro-L-arginine methyl ester hydrochloride (L-NAME)
L-Arg(NO2)-Ome·HCl
H-Aeg(NO2)-OMe.HCL
(S)-Methyl 2-amino-5-(3-nitroguanidino)-pentanoate hydrochloride
NG-nitro-L-Arg-OMe*HCl
L-Ornithine, N5-[imino(nitroamino)methyl]-, methyl ester, hydrochloride (1:1)
2-(4-amino-5-oxohexyl)-1-nitroguanidine hydrochloride

CAS:

51298-62-5

MF:

C7H16ClN5O4

MW:

269.69

EINECS:

257-116-1

Product Categories:

Inhibitors
Arginine [Arg, R]
Amino Acids and Derivatives
Amino hydrochloride
Nitric Oxide
Signalling
Amino Acids Derivatives
Amino Acids
Amino Acid Methyl Esters
Amino Acids (C-Protected)
Biochemistry

Mol File:

51298-62-5.mol

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N'-Nitro-L-arginine-methyl ester hydrochloride Chemical Properties

Melting point:: 157-161 °C (dec.)
alpha: 14.5 º (c=3, CH3OH)
refractive index: 15 ° (C=3, MeOH)
RTECS: RM2982570
storage temp.: -20°C
solubility: H₂O: 50 mg/mL
form: powder
color: white to off-white
Water Solubility: almost transparency
BRN: 3744166
InChIKey: QBNXAGZYLSRPJK-JEDNCBNOSA-N
CAS DataBase Reference: 51298-62-5(CAS DataBase Reference)

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Safety Information

Hazard Codes: Xn
Risk Statements: 22-36/37/38
Safety Statements: 22-24/25-36-26
WGK Germany: 3
HS Code: 29299090

MSDS

Language:English Provider:SigmaAldrich
Language:English Provider:ACROS

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N'-Nitro-L-arginine-methyl ester hydrochloride Usage And Synthesis

Description

L-NAME requires hydrolysis of the methyl ester by cellular esterases to become a fully functional inhibitor (L-NNA). L-NNA exhibits some selectivity for inhibition of neuronal and endothelial isoforms. It exhibits K_i values of 15 nM, 39 nM, and 4.4 μM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively. The reported K_i value for the inhibition of iNOS ranges from 4-65 μM. L-NAME inhibits cGMP formation in endothelial cells with an IC₅₀ of 3.1 μM (in the presence of 30 μM arginine) and reverses the vasodilation effects of acetylcholine in rat aorta rings with an EC₅₀ of 0.54 μM.

Chemical Properties

Crystalline

Uses

Nitroarginine Methyl Ester Hydrochloride is used in the synthesis of N/CD13 inhibitors playing an important role in tumor invasion, metastatsis and angiogenesis. Also used in the preparation of spirocyclic lactam as a type II’ β-turn inducer.

Definition

ChEBI: A hydrochloride obtained by combining Ngamma-nitro-L-arginine methyl ester with one equivalent of hydrochloric acid.

General Description

More soluble analog of arginine and a competitive, slowly reversible inhibitor of endothelial nitric oxide synthase (IC₅₀ = 500 nM). Causes a prolonged inhibition of acetylcholine-induced relaxation of rat aortic rings (IC₅₀ = 400 nM).

Biological Activity

NO synthase inhibitor.

Biochem/physiol Actions

Primary TargeteNOS

storage

Room temperature

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