Methyl N5-(imino(nitroamino)methyl)-L-ornithine monohydrochloride

Base Information

• Chemical Name: Methyl N5-(imino(nitroamino)methyl)-L-ornithine monohydrochloride
• CAS No.: 51298-62-5
• Molecular Formula: C7H16ClN5O4
• Molecular Weight: 269.688
• Hs Code.: 29299090
• European Community (EC) Number: 257-116-1
• UNII: TFX6A1PRZ1
• DSSTox Substance ID: DTXSID10199292
• Wikidata: Q27224955
• Pharos Ligand ID: 4XXV8R25ZVW7
• ChEMBL ID: CHEMBL1256014
• Mol file: 51298-62-5.mol

Synonyms:51298-62-5;L-NAME hydrochloride;H-Arg(NO2)-OMe.HCl;LNAME hydrochloride;H-Arg(NO2)-Ome HCl;L-NAME HCl;Methyl N5-(imino(nitroamino)methyl)-L-ornithine monohydrochloride;NG-Nitro-L-arginine methyl ester hydrochloride;L-NAME (hydrochloride);(S)-Methyl 2-amino-5-(3-nitroguanidino)pentanoate hydrochloride;Nomega-Nitro-L-arginine methyl ester hydrochloride;EINECS 257-116-1;TFX6A1PRZ1;CHEMBL1256014;N(gamma)-nitro-L-arginine methyl ester hydrochloride;methyl (2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoate;hydrochloride;(S)-Methyl 2-amino-5-(3-nitroguanidino)-pentanoate hydrochloride;SMR000326681;H-Arg(NO)-OMe HCl;Methyl N5-[imino(nitroamino)methyl]-L-ornithine monohydrochloride;NG-Nitro-L-arginine Methyl Ester, Hydrochloride;Arg(NO2)-OMe HCl;Arg(NO2)-OMe.HCl;L-NAME HCl;L-NAME monohydrochloride;UNII-TFX6A1PRZ1;N?-Nitro-L-arginine methyl ester hydrochloride;C7H15N5O4.ClH;C7H15N5O4.HCl;MLS001056504;MLS002153217;L-Nitro Arginine Methyl Ester;H-Ala(NO2)-OMe hydrochloride;H-Arg(NO2)-Ome hydrochloride;SCHEMBL18812631;DTXSID10199292;CHEBI:131182;C7-H15-N5-O4.Cl-H;Tox21_500848;HB1352;HY-18729A;methyl (2S)-2-amino-5-(3-nitrocarbamimidamido)pentanoate hydrochloride;MFCD00039052;s2877;AKOS015924237;L-Ornithine, N5-[imino(nitroamino)methyl]-, methyl ester,monohydrochloride;methyl (2S)-2-amino-5-(N'-nitrocarbamimidamido)pentanoate hydrochloride;CCG-222152;CS-5077;FD10543;LP00848;METHYL NW-NITRO-L-ARGININATE HCL;NCGC00261533-01;AS-17653;Methyl Nw-nitro-L-argininate hydrochloride;L-NG-Nitroarginine Methyl Ester (L-NAME);LS-183873;EU-0100848;N0661;EN300-204406;M03104;N 5751;methyl N(gamma)-nitro-L-argininate hydrochloride;N\'-Nitro-L-arginine-methyl ester hydrochloride;omega-nitro-l-arginine methyl ester hydrochloride;SR-01000597831;J-300042;n-omega-nitro-l-arginine methyl ester hydrochloride;SR-01000597831-1;Q27224955;N(gamma)-nitro-L-arginine methyl ester monohydrochloride;Z2009977611;N.OMEGA.-NITRO-L-ARGININE METHYL ESTER HYDROCHLORIDE;H-Arg(NO2)-OMe HCl;N-Nitro-L-arginine methyl ester hydrochloride

Chemical Property of Methyl N5-(imino(nitroamino)methyl)-L-ornithine monohydrochloride

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 3.83E-07mmHg at 25°C
• Melting Point: 157-161 °C
• Refractive Index: 15 ° (C=3, MeOH)
• Boiling Point: 383.5 °C at 760 mmHg
• Flash Point: 185.8 °C
• PSA: 146.05000
• LogP: 1.47960
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: almost transparency
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 269.0890817
• Heavy Atom Count: 17
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

N-Nitro-L-arginine methyl ester hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CCCN=C(N)N[N+](=O)[O-])N.Cl
• Isomeric SMILES: COC(=O)[C@H](CCCN=C(N)N[N+](=O)[O-])N.Cl
• Description: L-NAME requires hydrolysis of the methyl ester by cellular esterases to become a fully functional inhibitor (L-NNA). L-NNA exhibits some selectivity for inhibition of neuronal and endothelial isoforms. It exhibits Ki values of 15 nM, 39 nM, and 4.4 μM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively. The reported Ki value for the inhibition of iNOS ranges from 4-65 μM. L-NAME inhibits cGMP formation in endothelial cells with an IC50 of 3.1 μM (in the presence of 30 μM arginine) and reverses the vasodilation effects of acetylcholine in rat aorta rings with an EC50 of 0.54 μM.
• Uses: Nitroarginine Methyl Ester Hydrochloride is used in the synthesis of N/CD13 inhibitors playing an important role in tumor invasion, metastatsis and angiogenesis. Also used in the preparation of spirocyclic lactam as a type II’ β-turn inducer.

Technology Process of Methyl N5-(imino(nitroamino)methyl)-L-ornithine monohydrochloride

There total 7 articles about Methyl N5-(imino(nitroamino)methyl)-L-ornithine monohydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

methanol (67-56-1) + N-nitro-L-arginine (2149-70-4,13855-78-2,38733-00-5) → nitro-L-arginine methyl ester hydrochloride (51298-62-5)

Guidance literature:

With hydrogenchloride; for 0.25h; Heating;

DOI:10.1016/j.ejmech.2004.02.012

Reference yield: 90.0%

methanol (67-56-1) + N-nitro-L-arginine (2149-70-4,13855-78-2,38733-00-5) → L-NAME (50903-99-6,141968-19-6,51298-62-5,126265-24-5)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2010.01.075

Reference yield:

Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester (112208-06-7) → L-NAME (50903-99-6,141968-19-6,51298-62-5,126265-24-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

upstream raw materials:

methanol

N-nitro-L-arginine

L-arginine hydrochloride

Boc-Arg(NO₂)-OH

Downstream raw materials:

Tos-Gly-N^G-nitro-L-Arg-OMe

Tos-3,4(OH)2Phe-N^G-nitro-L-Arg-OMe

N-carbobenzoxy-L-prolyl-L-phenylalanyl-N^ω-nitro-L-arginine methyl ester

Boc-L-Phe-L-Arg^NO₂-OMe

Refernces

• 1、 Zhou, Yinjian,Zhao, Ming,Wu, Yingting,Li, Chunyu,Wu, Jianhui,Zheng, Meiqing,Peng, Li,Peng, Shiqi. "A class of novel Schiff's bases: Synthesis, therapeutic action for chronic pain, anti-inflammation and 3D QSAR analysis". experimental part. p. 2165 - 2172. Retrieved 2010/05/18.
• 2、 Mou, Jiajia,Fang, Hao,Jing, Fanbo,Wang, Qiang,Liu, Yingzi,Zhu, Huawei,Shang, Luqing,Wang, Xuejian,Xu, Wenfang. "Design, synthesis and primary activity evaluation of l-arginine derivatives as amino-peptidase N/CD13 inhibitors". scheme or table. p. 4666 - 4673. Retrieved 2009/12/01.