I8021

Sigma-Aldrich

L-N6-(1-Iminoethyl)lysine dihydrochloride

Synonym(s):
L-Lysine ω-acetamidine dihydrochloride, L-NIL dihydrochloride
Empirical Formula (Hill Notation):
C8H17N3O2 · 2 HCl
CAS Number:
Molecular Weight:
260.16
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

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)NCCCCC@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)

Packaging

10 mg in glass insert

Biochem/physiol Actions

Selective inhibitor of inducible nitric oxide synthase (iNOS).

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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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