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400600

Sigma-Aldrich

L-N⁵-(1-Iminoethyl)ornithine dihydrochloride

≥98% (TLC), solid, eNOS inhibitor, Calbiochem®

Synonym(s):

L-N⁵-(1-Iminoethyl)ornithine, Dihydrochloride, L-NIO, 2HCl

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About This Item

Empirical Formula (Hill Notation):
C7H15N3O2 · 2HCl
CAS Number:
159190-44-0
Molecular Weight:
246.13
UNSPSC Code:
12352209
NACRES:
NA.77

product name

L-N⁵-(1-Iminoethyl)ornithine, Dihydrochloride, A cell-permeable, more potent inhibitor of endothelial nitric oxide synthase compared to other arginine analogs such as L-NAME and L-NMMA.

Quality Level

100

Assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)

color

white

solubility

water: 1 mg/mL

shipped in

ambient

storage temp.

−20°C

InChI

1S/C7H15N3O2.2ClH/c1-5(8)10-4-2-3-6(9)7(11)12;;/h6H,2-4,9H2,1H3,(H2,8,10)(H,11,12);2*1H/t6-;;/m0../s1

InChI key

RYCMAAFECCXGHI-ILKKLZGPSA-N

General description

A cell-permeable, more potent inhibitor of endothelial nitric oxide synthase (eNOS; IC50 = 500 nM) compared to other arginine analogs such as L-NAME (Cat. No. 483125) and L-NMMA (Cat. No. 475886). Inhibits acetylcholine-induced relaxation of rat aorta rings (IC50 = 2 µM) and causes a dose-dependent increase in mean arterial blood pressure in the rat (EC50 = 19.5 mg/kg).
Cell permeable. Approximately five times more potent as an inhibitor of endothelial nitric oxide synthase (IC50 = 500 nM) than other arginine analogs, such as L-NAME (Cat. No. 483125) and L-NMMA (Cat. No. 475886). Inhibits acetylcholine induced relaxation of rat aorta rings (IC50 = 2 µM) and causes a dose-dependent increase in mean arterial blood pressure in the rat (EC50 = 19.5 mg/kg).

Biochem/physiol Actions

Cell permeable: yes
Primary Target
eNOS
Product does not compete with ATP.
Reversible: no
Target IC50: 500 nM against endothelial nitric oxide synthase (eNOS); 2 µM against acetylcholine-induced relaxation of rat aorta rings; EC50 = 19.5 mg/kg for a dose-dependent increase in mean arterial blood pressure in the rat

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Other Notes

Moore, W.M., et al. 1994. J. Med. Chem. 37, 3886.
Rees, D.D., et al. 1990. Br. J. Pharmacol.101, 746.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

400600-MG:
400600-20MG:

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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M Marquina et al.
The British journal of dermatology, 159(1), 68-76 (2008-05-15)
Pemphigus vulgaris (PV) is a blistering autoimmune disease characterized by IgG autoantibodies against desmoglein 3. Nitric oxide synthases (NOS) may contribute to the increase of inflammation in tissues by the generation of nitrotyrosine residues (NTR). To investigate whether the production

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