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I8021

Sigma-Aldrich

L-N6-(1-Iminoethyl)lysine dihydrochloride

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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

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)

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SML1158N5751V0882
vibrant-m

SML1158

(2S)-Hypusine dihydrochloride

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

water: 50 mg/mL, clear, colorless

solubility

H2O: 15 mg/mL, clear

solubility

H2O: 50 mg/mL

solubility

water: 50 mg/mL, clear, colorless to yellow

biological source

synthetic (organic)

biological source

-

biological source

synthetic

biological source

-

Gene Information

human ... NOS2(4843)

Gene Information

-

Gene Information

-

Gene Information

-

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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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