methyl (2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoate hydrochloride

• ChemBase ID: 104419
• Molecular Formular: C7H16ClN5O4
• Molecular Mass: 269.68604
• Monoisotopic Mass: 269.0890817
• SMILES: Cl.COC(=O)[C@@H](N)CCCNC(=N)N[N+](=O)[O-]
• Canonical SMILES: COC(=O)[C@H](CCCNC(=N)N[N+](=O)[O-])N.Cl
• InChI: InChI=1S/C7H15N5O4.ClH/c1-16-6(13)5(8)3-2-4-10-7(9)11-12(14)15;/h5H,2-4,8H2,1H3,(H3,9,10,11);1H/t5-;/m0./s1
• InChIKey: QBNXAGZYLSRPJK-JEDNCBNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoate hydrochloride; methyl (2S)-2-amino-5-(3-nitrocarbamimidamido)pentanoate hydrochloride
• IUPAC Traditional name: methyl (2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoate hydrochloride; methyl (2S)-2-amino-5-(3-nitrocarbamimidamido)pentanoate hydrochloride
• Synonyms: L-NAME hydrochloride; Nω-Nitro-L-arginine methyl ester hydrochloride; N-ω-NITRO-L-ARGININE METHYL ESTER; L-NAME HCl

Database IDs

• CAS Number: 51298-62-5
• EC Number: 257-116-1
• MDL Number: MFCD00039052
• Beilstein Number: 3744166
• PubChem SID: 162091664; 24278011; 24886447
• PubChem CID: 135193

CALCULATED PROPERTIES

• Acid pKa: 10.0243025
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -7.6532164
• LogD (pH = 7.4): -6.102299
• Log P: -2.5069947
• Molar Refractivity: 64.6743 cm^3
• Polarizability: 20.961002 Å^3
• Polar Surface Area: 143.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white to off-white powder
• Melting Point: 157-161 °C (dec.)
• Optical Rotation: [α]20/D +15.5±1°, c = 3% in methanol

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (TLC); ≥99.0% (AT)
• Salt Data: HCl
• Empirical Formula (Hill Notation): C7H15N5O4 · HCl

DETAILS

MP Biomedicals - 02155846

Hydrochloride Crystalline

Sigma Aldrich - N5751

Frequently Asked Questions
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Biochem/physiol Actions
An analog of arginine that inhibits NO production. It has multiple effects on the vascular system. Inhibits relaxation induced by acetylcholine and induces an increase in arterial blood pressure. Abolishes lecithinized superoxide dismutase induced vasodilation when used to pretreat aortic ring preparations of mice. Induces leukocyte adhesion and increases microvascular fluid and protein fluxes and permeability. It has also been used in many studies of learning and memory.