L-NAME HCl

Modify Date: 2024-01-02 18:42:52

L-NAME HCl Structure
L-NAME HCl structure
 Common Name L-NAME HCl
CAS Number 51298-62-5 Molecular Weight 269.686
Density N/A Boiling Point 383.5ºC at 760 mmHg
Molecular Formula C7H16ClN5O4 Melting Point 157-161 °C (dec.)
MSDS USA Flash Point 185.8ºC

 Use of L-NAME HCl


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.

 Names

Name N'-Nitro-L-arginine-methyl ester hydrochloride
Synonym More Synonyms

 L-NAME HCl Biological Activity

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
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)
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

 Precursor & DownStream

Precursor  0

DownStream  1

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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)
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