CAS 51298-62-5|L-NAME HCl
| Common Name | L-NAME HCl | ||
|---|---|---|---|
| CAS Number | 51298-62-5 | Molecular Weight | 269.686 |
| Density | / | Boiling Point | 383.5ºC at 760 mmHg |
| Molecular Formula | C7H16ClN5O4 | Melting Point | 157-161 °C (dec.) |
| MSDS | USA | Flash Point | 185.8ºC |
Names
| Name | N'-Nitro-L-arginine-methyl ester hydrochloride |
|---|---|
| Synonym | More Synonyms |
L-NAME HCl BiologicalActivity
| Description | L-NAME hydrochloride inhibits NOS with an IC50 of 70 μM. L-NAME is a precursor to NOS inhibitor L-NOARG which has an IC50 value of 1.4 μM. |
|---|---|
| Related Catalog | Signaling Pathways >>Immunology/Inflammation >>NO SynthaseResearch Areas >>Cancer |
| Target | IC50: 70 μM (NOS)[1] |
| In Vitro | L-arginine analogues are widely used inhibitors of nitric oxide synthase (NOS) activity, with Nw-nitro-L-arginine methyl ester (L-NAME) being at the head[2]. Freshly dissolved L-NAME is a 50 fold less potent inhibitor of purified brain NOS (mean IC50= 70 μM) than L-NOARG (IC50= 1.4 μM), but the apparent inhibitory potency of L-NAME approached that of L-NOARG upon prolonged incubation at neutral or alkaline pH. HPLC analyses reveal that NOS inhibition by L-NAME closely correlated with hydrolysis of the drug to L-NOARG[1]. |
| In Vivo | L-NAME infusion significantly decreases NKT-leukocyte level, tumor-necrosis factor (TNF)-alpha production by T-splenocytes and macrophages, and interferon-gamma production by T-leukocytes, monocytes, and T-splenocytes, as well as increased interleukin-6 production by T-leukocytes and monocytes and nitrate/nitrite production by T-leukocytes[3]. There is increasing evidence that nitric oxide may be involved in learning and memory. l-NAME produces a task-dependent impairment of fear extinction, and implies that nitric oxide signaling is involved in memory process of certain fear extinction tasks[4]. Chronic L-NAME administration induces cardiac hypertrophy in rodent models. Six weeks L-NAME administration induces significant cardiac hypertrophy compared to control hearts[5]. |
| Animal Admin | Rats: The purpose is to investigate dose effects of chronically infused NOS inhibitor, LNAME on the anabolism, inflammatory responses, and arginine metabolism in parenterally fed rats with cecal puncture-induced subacute peritonitis. Male Wistar rats (8-9 weeks old), initially weighing 250 g, are used in the study. Rats are divided into 4 groups and are administered total parenteral nutrition solutions with 0, 5 (low dose), 25 (medium dose), or 50 (high dose) mg/kg per day of L-NAME for 7 days[3]. Mice: 12-20 week old C57BL/6J mice (5 per group) are administered L-NAME (0.325mg/mL) in the drinking water. Hearts are excised at 1-day, 2-days, 5-days, 2-weeks or 6-weeks; or controls which received no L-NAME. Ventricular cross-sectional wall thickness and individual cardiac myocytes cross-sectional area and cardiomyocyte/nuclear ratio to determine cardiac hypertrophy. Immuno-histochemical staining for c-kit, sca-1 and BCRP undertaken[5]. |
| References | [1]. Pfeiffer S, et al. Inhibition of nitric oxide synthesis by NG-nitro-L-arginine methyl ester (L-NAME): requirement forbioactivation to the free acid, NG-nitro-L-arginine. Br J Pharmacol. 1996 Jul;118(6):1433-40. [2]. Kopincová J, et al. L-NAME in the cardiovascular system - nitric oxide synthase activator? Pharmacol Rep. 2012;64(3):511-20. [3]. Lo HC, et al. The Nitric Oxide Synthase Inhibitor NG-Nitro-L-Arginine Methyl Ester Diminishes the Immunomodulatory Effects of Parental Arginine in Rats with Subacute Peritonitis. PLoSOne. 2016 Mar 23;11(3):e0151973. [4]. Luo H, et al. Effect of nitric oxide synthase inhibitor L-NAME on fear extinction in rats: a task-dependent effect. Neurosci Lett. 2014 Jun 20;572:13-8. [5]. Ocsan RJ, et al. Chronic NG-nitro-l-arginine methyl ester (L-NAME) administration in C57BL/6J mice induces a sustained decrease in c-kit positive cells during development of cardiac hypertrophy. J Physiol Pharmacol. 2013 Dec;64(6):727-36. |
Chemical & Physical Properties
| Boiling Point | 383.5ºC at 760 mmHg |
|---|---|
| Melting Point | 157-161 °C (dec.) |
| Molecular Formula | C7H16ClN5O4 |
| Molecular Weight | 269.686 |
| Flash Point | 185.8ºC |
| Exact Mass | 269.089081 |
| PSA | 146.05000 |
| LogP | 1.47960 |
| Index of Refraction | 15 ° (C=3, MeOH) |
| InChIKey | QBNXAGZYLSRPJK-JEDNCBNOSA-N |
| SMILES | COC(=O)C(N)CCCN=C(N)N[N+](=O)[O-].Cl |
| Storage condition | 2~8°C |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Hazard Codes | Xn |
| Risk Phrases | R22 |
| Safety Phrases | S22-S24/25 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
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Synonyms
| LNAME hydrochloride |
| Nitro-L-arginine Methyl Ester Hydrochloride |
| MFCD00039052 |
| N(γ)-nitro-L-arginine methyl ester hydrochloride |
| N'-Nitro-L-arginine methyl ester hydrochloride |
| Methyl (E)-N-[amino(nitroamino)methylene]-L-ornithinate hydrochloride (1:1) |
| L-NAME hydrochloride |
| methyl (2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoate,hydrochloride |
| Nω-Nitro-L-arginine Methyl Ester Hydrochloride |
| NG-Nitro-L-arginine-methyl ester hydrochloride |
| EINECS 257-116-1 |
| L-Ornithine, N-[amino(nitroamino)methylene]-, methyl ester, (E)-, hydrochloride (1:1) |
| N-Nitro-L-Arginine methyl ester hydrochloride |
| (S)-Methyl 2-amino-5-(3-nitroguanidino)pentanoate hydrochloride |
| H-Arg(NO2)-Ome·Hcl |
| H-Arg(NO2)-Ome.HCl |
| N'-Nitro-L-arginine-methylester hydrochloride |
| L-NAME (hydrochloride) |
