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L-Arginine methyl ester dihydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

L-Arginine methyl ester is a protected form of L-Arginine. L-Arginine is a conditionally essential amino acid for humans and adult mammals as its requirements exceed production during certain developmental stages in life (such as pregnancy). L-Arginine also prevents blood toxicity from intravenous amino acid administration in humans.

Category

L-Amino Acids

Catalog number

BAT-003960

CAS number

26340-89-6

Molecular Formula

C7H16N4O2.2HCl

Molecular Weight

261.15

IUPAC Name

methyl (2S)-2-amino-5-(diaminomethylideneamino)pentanoate;dihydrochloride

Synonyms

L-Arginine, methyl ester, hydrochloride (1:2); L-Arginine, methyl ester, dihydrochloride; Arginine, methyl ester, dihydrochloride, L-; Arginine methyl ester dihydrochloride; Methyl (2S)-2-amino-5-guanidinopentanoate dihydrochloride; Methyl L-arginine dihydrochloride; N-α-L-Arginine methyl ester dihydrochloride

Related CAS

5629-84-5 (Deleted CAS) 2577-94-8 (free base)

Appearance

White powder

Purity

≥95%

Melting Point

192-194°C

Storage

Store at 2-8°C

InChI

InChI=1S/C7H16N4O2.2ClH/c1-13-6(12)5(8)3-2-4-11-7(9)10;;/h5H,2-4,8H2,1H3,(H4,9,10,11);2*1H/t5-;;/m0../s1

InChI Key

XQYZOBNLCUAXLF-XRIGFGBMSA-N

Canonical SMILES

COC(=O)C(CCCN=C(N)N)N.Cl.Cl

L-Arginine methyl ester dihydrochloride is a chemical compound derived from the amino acid L-arginine. It is characterized by the addition of a methyl ester group and the presence of two chloride ions. This compound is primarily used in scientific research and industries due to its unique properties, such as its ability to donate nitric oxide (NO) and its role in the biosynthesis of proteins. Given its molecular structure, L-Arginine methyl ester dihydrochloride is a valuable reagent in biochemical studies and has multiple industrial applications.

One of the key industrial applications of L-Arginine methyl ester dihydrochloride is in pharmaceuticals. This compound is utilized in the development of drugs that target cardiovascular diseases due to its vasodilatory effects, which help in improving blood flow and reducing hypertension. Additionally, its role in protein metabolism makes it a candidate for various therapeutic agents designed to enhance recovery and muscle building in patients with specific medical conditions.

Another important application of L-Arginine methyl ester dihydrochloride is in the cosmetics industry. Its ability to promote collagen production and improve skin elasticity makes it a popular ingredient in many anti-aging and skin care products. The compound is also used in formulations designed to promote wound healing, owing to its role in nitric oxide production, which is crucial for the repair and regeneration of skin tissues.

L-Arginine methyl ester dihydrochloride is also significant in the field of nutritional supplements. Bodybuilders and athletes often use this compound to improve performance and muscle growth. It supplements the endogenous production of L-arginine, leading to enhanced protein synthesis and increased nitric oxide levels, which can improve endurance, reduce fatigue, and expedite muscle recovery.

Finally, L-Arginine methyl ester dihydrochloride finds its use in agricultural sciences. This compound can be applied as a growth enhancer in plants due to its ability to stimulate nitrate uptake and metabolism. By boosting nitric oxide levels within plant tissues, it supports better growth rates and improved resistance to environmental stressors, making it valuable for enhancing crop yields and productivity.

1.Small interfering RNA for cancer treatment: overcoming hurdles in delivery

Acta Pharm Sin B. 2020 Nov;10(11):2075-2109. doi: 10.1016/j.apsb.2020.10.005.

In many ways, cancer cells are different from healthy cells. A lot of tactical nano-based drug delivery systems are based on the difference between cancer and healthy cells. Currently, nanotechnology-based delivery systems are the most promising tool to deliver DNA-based products to cancer cells. This review aims to highlight the latest development in the lipids and polymeric nanocarrier for siRNA delivery to the cancer cells. It also provides the necessary information about siRNA development and its mechanism of action. Overall, this review gives us a clear picture of lipid and polymer-based drug delivery systems, which in the future could form the base to translate the basic siRNA biology into siRNA-based cancer therapies.

2.Effects of NG-nitro-L-arginine methyl ester on regional haemodynamic responses to MgSO4 in conscious rats

Br J Pharmacol. 1994 Jan;111(1):325-31. doi: 10.1111/j.1476-5381.1994.tb14063.x.

1. We assessed regional haemodynamic responses to the vasodilator, MgSO4, in the absence and presence of the nitric oxide synthase inhibitor, NG-nitro-L-arginine methyl ester (L-NAME), in conscious chronically instrumented Long Evans rats (n = 9). 2. MgSO4 (loading dose 220 mumol kg-1 min-1 for 7 min, maintenance dose 56 mumol kg-1 min-1 for 7 min), alone, caused slight bradycardia and hypotension accompanied by reductions in renal and mesenteric flows, but a marked hyperaemic vasodilatation in the hindquarters (flow, delta 54 +/- 6%, vascular conductance, delta 77 +/- 5%). 3. L-NAME (183 nmol kg-1 min-1) caused hypertension (29 +/- 2 mmHg) accompanied by bradycardia (-51 +/- 6 beats min-1) and reductions in flow and vascular conductance in the renal (-18 +/- 4% and -35 +/- 3%, respectively), mesenteric (-35 +/- 3% and -49 +/- 3%, respectively), and hindquarters (-26 +/- 3% and -42 +/- 3%, respectively) vascular beds. In the presence of L-NAME, the hypotensive and bradycardic effects of MgSO4 were still apparent, but its hindquarters hyperaemic vasodilator effect was significantly attenuated. 4. In order to determine if the inhibitory action of L-NAME on the hindquarters hyperaemic vasodilator action of MgSO4 was a non-specific effect, due to the change in baseline conditions caused by L-NAME, we also examined responses to MgSO4 in the presence of endothelin-1 (12.5 pmol kg-1 min-1) or angiotensin II (50 pmol kg-1 min-1). In the presence of either peptide, the overall effects of MgSO4 on hindquarters flow and vascular conductance were unchanged. 5. In a separate experiment (n = 8) we determined that the inhibitory effect of L-NAME on the hyperaemic vasodilator response to MgSO4 was prevented by L-arginine, and also demonstrated that the Beta2-adrenoceptor antagonist, ICI 118551, caused significant inhibition of the hindquarters haemodynamic effects of MgSO4.6. We conclude that the hindquarters haemodynamic effects of MgSO4 in conscious rats involve a substantial L-NAME-sensitive component which depends on activation of Beta2-adrenoceptors, probably asa consequence of adrenal medullary adrenaline release.

3.A newly synthesized compound, 4'-geranyloxyferulic acid-N(omega)-nitro-L-arginine methyl ester suppresses inflammation-associated colorectal carcinogenesis in male mice

Int J Cancer. 2014 Aug 15;135(4):774-84. doi: 10.1002/ijc.28718.

We previously reported the cancer chemopreventive activity of 4'-geranyloxyferulic acid (GOFA, Miyamoto et al., Nutr Cancer 2008; 60:675-84) and a β-cyclodextrin inclusion compound of GOFA (Tanaka et al., Int J Cancer 2010; 126:830-40) in colitis-related colorectal carcinogenesis. In our study, the chemopreventive effects of a newly synthesized GOFA-containing compound, GOFA-N(omega)-nitro-L-arginine methyl ester (L-NAME), which inhibits inducible nitric oxide (iNOS) and cyclooxygenase-2 (COX) enzymes, were investigated using a colitis-associated mouse colorectal carcinogenesis model with azoxymethane (AOM) and dextran sodium sulfate (DSS). The dietary administration of GOFA-L-NAME after the AOM and DSS treatments significantly reduced the multiplicity of adenocarcinomas (inhibition rates: 100 ppm, 84%, p < 0.001; 500 ppm, 94%, p < 0.001) compared with the AOM + DSS group. Dietary GOFA-L-NAME significantly decreased the proliferation (p < 0.001) and increased the apoptosis (p < 0.001) of colonic adenocarcinoma cells. A subsequent short-term experiment revealed that dietary GOFA-L-NAME decreased the mRNA expression of inflammatory enzymes, such as iNOS and COX-2, and proinflammatory cytokines, such as tumor necrosis factor-α, interleukin (IL)-1β, IL-6 and macrophage inflammatory protein (MIP)-2 in the colonic mucosa of mice that received 1.5% DSS in their drinking water for 7 days. Our findings indicate that GOFA-L-NAME is able to inhibit colitis-associated colon carcinogenesis by modulating inflammation, proliferation, apoptosis and the expression of proinflammatory cytokines in mice.