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I8021

Sigma-Aldrich

L-N6-(1-Iminoethyl)lysine dihydrochloride

Synonym(s):

L-Lysine ω-acetamidine dihydrochloride, L-NIL dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C8H17N3O2 · 2 HCl
CAS Number:
159190-45-1
Molecular Weight:
260.16
MDL number:
MFCD00270890
UNSPSC Code:
12352209
PubChem Substance ID:
24278827
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥97% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl.Cl.CC(=N)NCCCC[C@H](N)C(O)=O

InChI

1S/C8H17N3O2.2ClH/c1-6(9)11-5-3-2-4-7(10)8(12)13;;/h7H,2-5,10H2,1H3,(H2,9,11)(H,12,13);2*1H/t7-;;/m0../s1

InChI key

OQIBCXRAFAHXMM-KLXURFKVSA-N

Gene Information

human ... NOS2(4843)

Application

L-N6-(1-Iminoethyl)lysine dihydrochloride has been used as an inducible nitric oxide synthase (iNOS) inhibitor:
  • to study its effects on leptin-induced modulation of fibronectin type III domain-containing five (FNDC5)/irisin in myocytes and fat cells of murine
  • to study its effects on leptin-induced inflammation in hepatocytes
  • to block the production of nitric oxide in mice bone marrow mesenchymal stromal cells (BMSCs)

Biochem/physiol Actions

Selective inhibitor of inducible nitric oxide synthase (iNOS).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Sigma-Aldrich

400600

L-N⁵-(1-Iminoethyl)ornithine, Dihydrochloride

W M Moore et al.
Journal of medicinal chemistry, 37(23), 3886-3888 (1994-11-11)
L-N6-(1-Iminoethyl)lysine (L-NIL) has been synthesized and is shown to be both a potent and selective inhibitor of mouse inducible nitric oxide synthase (miNOS). L-NIL has an IC50 of 3.3 microM for miNOS compared to an IC50 of 92 microM for
Sara Becerril et al.
Genes, 10(3) (2019-03-02)
iNOS deficiency in ob/ob mice improved liver inflammation and ECM remodeling-related genes, decreasing fibrosis, and metabolic dysfunction. The activation of iNOS by leptin is necessary for the synthesis and secretion of TNC in hepatocytes, suggesting an important role of this
Nikolai V Gorbunov et al.
Journal of cellular and molecular medicine, 19(5), 1133-1150 (2015-02-28)
The bone marrow stroma constitutes the marrow-blood barrier, which sustains immunochemical homoeostasis and protection of the haematopoietic tissue in sequelae of systemic bacterial infections. Under these conditions, the bone marrow stromal cells affected by circulating bacterial pathogens shall elicit the
Jérémy Postat et al.
Immunity, 49(4), 654-665 (2018-09-30)
Recruitment of immune cells with antimicrobial activities is essential to fight local infections but has the potential to trigger immunopathology. Whether the immune system has the ability to sense inflammation intensity and self-adjust accordingly to limit tissue damage remains to be
A Rodríguez et al.
International journal of obesity (2005), 39(3), 397-407 (2014-09-10)
BACKGROUND/OBJETIVES: Obese leptin-deficient ob/ob mice exhibit high adiposity and reduced muscle mass with leptin replacement promoting weight loss and inducing muscle accretion through PGC-1α-dependent mechanisms. Our aim was to analyze in vivo and in vitro the effect of leptin on
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