(2S)-2-amino-5-(1-methylcarbamimidamido)pentanoic acid; acetic acid

• ChemBase ID: 104323
• Molecular Formular: C9H20N4O4
• Molecular Mass: 248.2795
• Monoisotopic Mass: 248.14845514
• SMILES: CNC(=N)NCCC[C@H](N)C(=O)O.CC(=O)O
• Canonical SMILES: CC(=O)O.CNC(=N)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H16N4O2.C2H4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13;1-2(3)4/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);1H3,(H,3,4)/t5-;/m0./s1
• InChIKey: IKPNWIGTWUZCKM-JEDNCBNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(1-methylcarbamimidamido)pentanoic acid; acetic acid
• IUPAC Traditional name: acetic acid; delta-N-methylarginine
• Synonyms: N^G-METHYL-L-ARGININE; Nω-Methyl-L-arginine acetate salt; L-NMMA; N5-(Methylamidino)-L-ornithine acetate salt; NG-Monomethyl-L-arginine acetate salt; NG-Methyl-L-arginine acetate salt; N5-[Imino(methylamino)methyl]-L-ornithine Acetate; ANO 1020; Tilarginine Acetate; NG-Monomethyl-L-arginine Acetate

Database IDs

• CAS Number: 53308-83-1
• MDL Number: MFCD00069311
• Beilstein Number: 6674255
• PubChem SID: 24278043; 162091446
• PubChem CID: 135242

CALCULATED PROPERTIES

• Acid pKa: 2.482201
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.788655
• LogD (pH = 7.4): -4.5643816
• Log P: -2.8717082
• Molar Refractivity: 58.6977 cm^3
• Polarizability: 18.727592 Å^3
• Polar Surface Area: 111.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL, clear, colorless; Methanol; Water
• Apperance: White Solid
• Melting Point: 179-182°C; 182-190°C

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• Storage Warning: Store at - 5°C; Desiccate Recommended
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... NOS1(4842), NOS2(4843), NOS3(4846)mouse ... Nos2(18126)rat ... Nos1(24598), Nos2(24599)

Product Information

• Purity: ≥95% (HPLC); ≥98% (TLC)
• Impurities: ≤3.5% water
• Empirical Formula (Hill Notation): C7H16N4O2 · C2H4O2

DETAILS

MP Biomedicals - 02155470

Acetate Salt Endothelium-derived relaxing factor inhibitor.

Sigma Aldrich - M7033

Biochem/physiol Actions
Endothelium-derived relaxing factor inhibitor. Inhibits the generation of NO from arginine.

Sigma Aldrich - 65825

Other Notes
Endothelium-derived relaxing factor inhibitor1

Toronto Research Chemicals - M565000

A potent inhibitor of NO synthase of adrenal glands, brain, and vascular endothelial cells.

REFERENCES

• Sakuma, I., et al., Proc. Nat. Acad. Sci. USA, 85: 8664 (1988).
• Rees, D.D., et al.: Br. J. Pharmacol., 101, 746 (1990)
• McCall, T.B., et al.: Br. J. Pharmacol., 102, 234 (1990)
• Olken, N.M., et al.: Biochem. and Biophys. Res. Commun., 177, 2, 828 (1991)