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

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