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2480-28-6

2480-28-6 | L-Arginine, N2-methyl-

CAS No: 2480-28-6 Catalog No: AG002PHF MDL No:

Product Description

Catalog Number:
AG002PHF
Chemical Name:
L-Arginine, N2-methyl-
CAS Number:
2480-28-6
Molecular Formula:
C7H16N4O2
Molecular Weight:
188.2275
IUPAC Name:
(2S)-5-(diaminomethylideneamino)-2-(methylamino)pentanoic acid
InChI:
InChI=1S/C7H16N4O2/c1-10-5(6(12)13)3-2-4-11-7(8)9/h5,10H,2-4H2,1H3,(H,12,13)(H4,8,9,11)/t5-/m0/s1
InChI Key:
NTWVQPHTOUKMDI-YFKPBYRVSA-N
SMILES:
CN[C@H](C(=O)O)CCCNC(=N)N
UNII:
88RBJ4ZE9R

Properties

Complexity:
189  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
188.127g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
188.231g/mol
Monoisotopic Mass:
188.127g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
114A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.7  

Literature

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Systemic inflammation induces apoptosis with variable vulnerability of different brain regions. Journal of chemical neuroanatomy 20051001
Adrenomedullin causes coronary vasodilation in humans: effects of inhibition of nitric oxide synthesis. Journal of cardiovascular pharmacology 20051001
Mechanisms of adenosine-induced renal vasodilatation in hypertensive patients. Journal of hypertension 20050901
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Effects of isoprostane on tubuloglomerular feedback: roles of TP receptors, NOS, and salt intake. American journal of physiology. Renal physiology 20050401
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Prophylactic high-dose N(omega)-monomethyl-L-arginine prevents the late cardiac dysfunction associated with lethal tumor necrosis factor-alpha challenge in dogs. Shock (Augusta, Ga.) 20050301
Nitric oxide inhibition of homocysteine-induced human endothelial cell apoptosis by down-regulation of p53-dependent Noxa expression through the formation of S-nitrosohomocysteine. The Journal of biological chemistry 20050218
eNOS, nNOS, cGMP and protein kinase G mediate the inhibitory effect of pancreastatin, a chromogranin A-derived peptide, on growth and proliferation of hepatoma cells. Regulatory peptides 20050215
PRMT7, a new protein arginine methyltransferase that synthesizes symmetric dimethylarginine. The Journal of biological chemistry 20050204
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Effects of soy isoflavones on endothelial function in healthy postmenopausal women. Menopause (New York, N.Y.) 20050101
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Renal blood flow in sepsis. Critical care (London, England) 20050101
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Reducing arginase activity via dietary manganese deficiency enhances endothelium-dependent vasorelaxation of rat aorta. Experimental biology and medicine (Maywood, N.J.) 20041201
Low sodium diet inhibits the local counter-regulator effect of angiotensin-(1-7) on angiotensin II. Journal of hypertension 20041201
Hemodynamic and sympathoadrenal responses to mental stress during nitric oxide synthesis inhibition. American journal of physiology. Heart and circulatory physiology 20041101
Glutamate induces apoptosis in anterior pituitary cells through group II metabotropic glutamate receptor activation. Endocrinology 20041001
beta-Adrenoceptor-mediated, nitric-oxide-dependent vasodilatation is abnormal in early hypertension: restoration by L-arginine. Journal of hypertension 20041001
Contribution of interaction between nitric oxide and cyclooxygenases to the production of prostaglandins in carrageenan-induced inflammation. Anesthesiology 20041001
Simultaneous determination of L-arginine and its mono- and dimethylated metabolites in human plasma by high-performance liquid chromatography-mass spectrometry. Analytical and bioanalytical chemistry 20041001
Inhibition of l-arginine transport in platelets by asymmetric dimethylarginine and N-monomethyl-l-arginine: effects of arterial hypertension. Clinical and experimental pharmacology & physiology 20041001
Nitric oxide pathway in the nucleus raphe magnus modulates hypoxic ventilatory response but not anapyrexia in rats. Brain research 20040813
Functional role of the Na+/H+ exchanger in the regulation of cerebral arteriolar tone in rats. Journal of neurosurgery 20040801
Accumulated endogenous nitric oxide synthase inhibitors in inhibiting urethral relaxation following estrogen supplementation in ovariectomized rabbits. The Journal of urology 20040701
Involvement of increased arginase activity in impaired cavernous relaxation with aging in the rabbit. The Journal of urology 20040701
The cardiovascular effects of nitric oxide and carbon monoxide in the nucleus tractus solitarii of rats. Journal of hypertension 20040601
Neuropeptide Y enhances permeability across a rat aortic endothelial cell monolayer. American journal of physiology. Heart and circulatory physiology 20040301
Cerivastatin inhibits proliferation of interleukin-1 beta-induced rat mesangial cells by enhanced formation of nitric oxide. European journal of pharmacology 20040206
Effects of imidapril, an angiotensin-converting enzyme inhibitor, on insulin sensitivity and responsiveness in streptozotocin-induced diabetic rats. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20040101
Ability of T cell subsets and their soluble mediators to modulate the replication of Mycobacterium bovis in bovine macrophages. Cellular immunology 20040101
Dimethylarginine dimethylaminohydrolase regulates nitric oxide synthesis: genetic and physiological evidence. Circulation 20031216
Role of nitric oxide, reactive oxygen species, and p38 MAP kinase in the regulation of human chondrocyte apoptosis. Journal of cellular physiology 20031201
Novel roles for palmitoylation of Ras in IL-1 beta-induced nitric oxide release and caspase 3 activation in insulin-secreting beta cells. Biochemical pharmacology 20031101
Nitric oxide produced by murine dendritic cells is cytotoxic for intracellular Salmonella enterica sv. Typhimurium. Scandinavian journal of immunology 20031101
Interleukin-6 protects MIN6 beta cells from cytokine-induced apoptosis. Annals of the New York Academy of Sciences 20031101
Falcarindiol inhibits nitric oxide-mediated neuronal death in lipopolysaccharide-treated organotypic hippocampal cultures. Neuroreport 20031027
Excessive production of nitric oxide induces the neuronal cell death in lipopolysaccharide-treated rat hippocampal slice culture. Neuroscience letters 20030925
The HMG-CoA reductase inhibitor cerivastatin enhances the nitric oxide bioavailability of the endothelium. Journal of cardiovascular pharmacology 20030901
Effects of overexpression of dimethylarginine dimethylaminohydrolase on tumor angiogenesis assessed by susceptibility magnetic resonance imaging. Cancer research 20030815
Melatonin attenuates alpha-adrenergic-induced contractions by increasing the release of vasoactive intestinal peptide in isolated rat penile bulb. Urological research 20030801
Nitric oxide in the rostral ventrolateral medulla modulates hyperpnea but not anapyrexia induced by hypoxia. Brain research 20030711
Heme oxygenase-1 induction by endogenous nitric oxide: influence of intracellular glutathione. FEBS letters 20030710
Kidney transplantation improves endothelium-dependent vasodilation in patients with endstage renal disease. Transplantation 20030615
Statins induce angiogenesis, neurogenesis, and synaptogenesis after stroke. Annals of neurology 20030601
AT1-receptor antagonism improves endothelial function in coronary artery disease by a bradykinin/B2-receptor-dependent mechanism. Hypertension (Dallas, Tex. : 1979) 20030501
Hyperalgesia induced by Asp49 and Lys49 phospholipases A2 from Bothrops asper snake venom: pharmacological mediation and molecular determinants. Toxicon : official journal of the International Society on Toxinology 20030501
Platelet-activating factor synthesis by neutrophils, monocytes, and endothelial cells is modulated by nitric oxide production. Shock (Augusta, Ga.) 20030401
Effect of high-dose statin treatment on plasma concentrations of endogenous nitric oxide synthase inhibitors. Journal of cardiovascular pharmacology 20030201
Interleukin-1beta inhibits ATP-induced protein kinase B activation in renal mesangial cells by two different mechanisms: the involvement of nitric oxide and ceramide. British journal of pharmacology 20030201
Regulation of NF-kappaB activation by protein phosphatase 2B and NO, via protein kinase A activity, in human monocytes. Nitric oxide : biology and chemistry 20030201
HIF-1 alpha protein as a target for S-nitrosation. FEBS letters 20030130
Renal hemodynamic and ureteral pressure changes in response to ureteral obstruction: the role of nitric oxide. The Journal of urology 20030101
House dust mite Dermatophagoides farinae augments proinflammatory mediator productions and accessory function of alveolar macrophages: implications for allergic sensitization and inflammation. Journal of immunology (Baltimore, Md. : 1950) 20030101
Branched chain fatty acids induce nitric oxide-dependent apoptosis in vascular smooth muscle cells. The Journal of biological chemistry 20021220
Prostaglandins are involved in acetylcholine- and 5-hydroxytryptamine-induced, nitric oxide-mediated vasodilatation in human forearm. Journal of cardiovascular pharmacology 20021201
C-reactive protein relaxes human vessels in vitro. Arteriosclerosis, thrombosis, and vascular biology 20021101
Lipopolysaccharide-induced metastatic growth is associated with increased angiogenesis, vascular permeability and tumor cell invasion. International journal of cancer 20021010
Dimethylarginine dimethylaminohydrolase I enhances tumour growth and angiogenesis. British journal of cancer 20020909
Role of propofol and its solvent, intralipid, in nitric oxide-induced peripheral vasodilatation in dogs. British journal of anaesthesia 20020901
Changes in blood pressure and heart rate by repetitive transcranial magnetic stimulation in rats. Neuroscience letters 20020823
Superoxide activates constitutive nitric oxide synthase in a brain particulate fraction. Biochemical and biophysical research communications 20020816
Activated factor XII levels and factor XII 46C>T genotype in relation to coronary artery calcification in patients with type 1 diabetes and healthy subjects. Atherosclerosis 20020801
Peroxynitrite and the regulation of Na(+),K(+)-ATPase activity by angiotensin II in the rat proximal tubule. Nitric oxide : biology and chemistry 20020801
Genotoxicity associated with NO production in macrophages and co-cultured target cells. Free radical biology & medicine 20020701
Regulation by reactive oxygen species of interleukin-1beta, nitric oxide and prostaglandin E(2) production by human chondrocytes. Osteoarthritis and cartilage 20020701
Nitric oxide and blood pressure in mice lacking extracellular-superoxide dismutase. Free radical research 20020701
High glucose induced nuclear factor kappa B mediated inhibition of endothelial cell migration. Atherosclerosis 20020601
Glioma-associated hyaluronan induces apoptosis in dendritic cells via inducible nitric oxide synthase: implications for the use of dendritic cells for therapy of gliomas. Cancer research 20020501
Host systemic and local nitric oxide levels do not correlate with rejection of pig proislet xenografts in mice. Xenotransplantation 20020501
Expression of TGF-betas and their receptors is differentially modulated by reactive oxygen species and nitric oxide in human articular chondrocytes. Osteoarthritis and cartilage 20020501
Determination of arginine, asymmetric dimethylarginine, and symmetric dimethylarginine in human plasma and other biological samples by high-performance liquid chromatography. Analytical biochemistry 20020415
Effect of inhibitors of nitric oxide synthase on acetaminophen-induced hepatotoxicity in mice. Nitric oxide : biology and chemistry 20020301
Specific expression of Bax-omega in pancreatic beta-cells is down-regulated by cytokines before the onset of apoptosis. Endocrinology 20020101
Effect of pravastatin on responsiveness to N-monomethyl-L-arginine in patients with hypercholesterolaemia. Atherosclerosis 20020101
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Preservation of venous endothelial function in the forearm venous capacitance bed of patients with chronic heart failure despite arterial endothelial dysfunction. Journal of the American College of Cardiology 20010315
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