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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.

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Synonym(s):
L-N⁵-(1-Iminoethyl)ornithine, Dihydrochloride, L-NIO, 2HCl
Empirical Formula (Hill Notation):
C7H15N3O2 · 2HCl
CAS Number:
Molecular Weight:
246.13

Quality Level

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

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This Item
311203311204472804
assay

≥98% (TLC)

assay

≥98% (TLC)

assay

≥97% (HPLC)

assay

≥95% (HPLC)

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

solubility

water: 1 mg/mL

solubility

water: 50 mg/mL

solubility

water: 50 mg/mL

solubility

water: 50 mg/mL

storage condition

OK to freeze, desiccated (hygroscopic)

storage condition

OK to freeze, desiccated (hygroscopic)

storage condition

OK to freeze, desiccated (hygroscopic)

storage condition

OK to freeze, desiccated (hygroscopic)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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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