Name | H-Arg(NO2)-Ome.HCl |
Synonyms | L-Arg(NO2)-Ome·HCl H-Aeg(NO2)-OMe.HCL H-Arg(NO2)-OMe·HCl H-Arg(NO2)-Ome.HCl L-NAME Hydrochloride NG-nitro-L-Arg-OMe*HCl L-NG-Nitroarginine Methyl Ester (L-NAME) N'-Nitro-L-arginine-methyl ester hydrochloride NG-Nitro-L-arginine-methyl Ester Hydrochloride 2-(4-amino-5-oxohexyl)-1-nitroguanidine hydrochloride Nω-Nitro-L-arginine methyl ester hydrochloride (L-NAME) (S)-Methyl 2-amino-5-(3-nitroguanidino)-pentanoate hydrochloride |
CAS | 51298-62-5 |
EINECS | 257-116-1 |
InChI | InChI=1/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 |
InChIKey | QBNXAGZYLSRPJK-JEDNCBNOSA-N |
Molecular Formula | C7H16ClN5O4 |
Molar Mass | 269.69 |
Melting Point | 157-161°C (dec.) |
Boling Point | 410.7°C at 760 mmHg |
Specific Rotation(α) | 14.5 º (c=3, CH3OH) |
Flash Point | 202.2°C |
Water Solubility | almost transparency |
Solubility | H2O: 50mg/mL |
Vapor Presure | 3.83E-07mmHg at 25°C |
Appearance | Crystalline powder |
Color | white to off-white |
BRN | 3744166 |
Storage Condition | -20°C |
Refractive Index | 15 ° (C=3, MeOH) |
MDL | MFCD00039052 |
Use | An arginine analog that inhibits NO production. In multiple effects on the vascular system. Inhibits acetylcholine-induced relaxation and induces increased arterial blood pressure. |
In vitro study | NG-nitro-L-arginine methyl ester (L-NAME; 0.1-100 mM) concentration-dependent inhibition of Ca 2 (+)-dependent endothelial NO synthase in porcine aorta. L-NAME causes endothelium-dependent contraction in aortic rings and inhibition of acetylcholine (ACh)-induced vascular endothelium-dependent relaxation. In another study, rMC-1 cells or BREC were significantly less active in 25 mM glucose than in 5 mM glucose, and this cell death was l-NAME suppressed in both cell types. |
In vivo study | L-NAME(0.03-300 mg kg-1, I. v.) induced a dose-dependent increase in mean systemic arterial blood pressure accompanied by bradycardia. L-NAME (100 mg kg-1, I. v.) significantly inhibited the hypotensive response to Ach and bradykinin. The L-NAME-induced increase in blood pressure and bradycardia were L-arginine (30-100 mg kg-1, I. v.) dose-dependently reversed. |
Hazard Symbols | Xn - Harmful |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | RM2982570 |
HS Code | 29299090 |
Reference Show more | 1. Wei Chengke, Liu Shiyin, Li Yingdong. Protective effect of Angelica sinensis volatile oil on vascular endothelial injury induced by L-Nitroarginine methyl ester in hypertensive rats [J]. Chinese herbal medicines, 2017,40(04):937-940. 2. Li Jianmei, Liu Hui, Wang Qing, et al. Antihypertensive effect of Sophora Japonica on hypertensive rats [J]. Journal of Jining Medical University, 2011, 34(005):319-320. 3. Song Yan, Yang Xue, Xu Bohui, etc. Anti-asthmatic activity of vitexin in guinea pigs [J]. Modern medicine and health, 2014, 30(006):801-802. 4. Wei Jie, Li Yanjiao, Chen Xiaojun, etc. Protective effect of total flavonoids of Huangqi on aortic injury in type 2 diabetic rats with atherosclerosis [J]. Chinese traditional medicines, 2018, 040(007):1458-1463. 5. Wei Jie, Li Yanjiao, Chen Xiaojun, etc. Effect of total flavonoids of Huangqi on insulin resistance in rats with type 2 diabetes mellitus and atherosclerosis [J]. Chinese patent medicine, 2018, v.40(09):165-168. 6. Xian Jingping Wang Yong Ma Huiling. Involvement of Nitric oxide signaling pathway in cadmium tolerance of Kentucky bluegrass [J]. Journal of Grassland Science 2019 v.27(06):122-131. 7. Chen Zhongquan, Fu Chunru, Fu Fengqin, et al. Effects of piperine on arecoline-induced motility of isolated small intestinal smooth muscle in rabbits [J]. World Chinese Journal of Gastroenterology, 2019, 27(01):20-28. 8. [IF = 2.776] Jianchun Huang et al."The Effects." Plos One. 2014 Mar;9(3): c91834 9. [IF = 5.279] Yanbo Huang et al."Novel ACE Inhibition criteria and Effects on HUVECs." J Agr Food Chem. 2021;69(8):2412-2421 10. [IF=4.225] Li Bo et al."Hypertensive Rats Treated Chronically With Nω-Nitro-L-Arginine Methyl Ester (L-NAME) Induced Disorder of Hepatic Fatty Acid Metabolism and Intestinal Pathophysiology."Front Pharmacol. 2020 Jan;0:1677 11. [IF=5.811] Zhenchao Niu et al."Evaluation of Potential Herb-Drug Interactions Between Shengmai Injection and Losartan Potassium in Rat and In Vitro."Frontiers in Pharmacology. 2022; 13: 878526 |
biological activity | L-NAME HCl (NG-Nitroarginine methyl ester, N-Nitro-L-arginine methylester) is a non-selective nitric oxide synthase inhibitor. The Ki values for nNOS (cattle source), eNOS (human source) and iNOS (mouse source) are 15nM, 39 nM and 4.4 μM respectively. |
Target | Value |
nNOS (Cell-free assay) | 15 nM(Ki) |
eNOS (Cell-free assay) | 39 nM(Ki) |
Use | An arginine analog that inhibits NO production. In multiple effects on the vascular system. Inhibits acetylcholine-induced relaxation and induces increased arterial blood pressure. |