NG-Nitroarginine methyl ester

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MedKoo CAT#: 597661

CAS#: 50903-99-6

Description: NG-Nitroarginine methyl ester is a non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.


Price and Availability

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Pricing updated 2020-10-29. Prices are subject to change without notice.

NG-Nitroarginine methyl ester is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597661
Name: NG-Nitroarginine methyl ester
CAS#: 50903-99-6
Chemical Formula: C7H15N5O4
Exact Mass: 233.1124
Molecular Weight: 233.22
Elemental Analysis: C, 36.05; H, 6.48; N, 30.03; O, 27.44


Synonym: NG-Nitroarginine methyl ester; L-NAME;

IUPAC/Chemical Name: methyl Nw-nitro-L-argininate

InChi Key: KCWZGJVSDFYRIX-YFKPBYRVSA-N

InChi Code: InChI=1S/C7H15N5O4/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)/t5-/m0/s1

SMILES Code: N[C@@H](CCCNC(N[N+]([O-])=O)=N)C(OC)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

1: Güney HZ, Görgün CZ, Tunçtan B, Uludağ O, Hodoğlugil U, Abacioğlu N, Zengil H. Circadian-rhythm-dependent effects of L-NG-nitroarginine methyl ester (L-NAME) on morphine-induced analgesia. Chronobiol Int. 1998 May;15(3):283-9. PubMed PMID: 9653581.

2: Tsuda K. Letter by Tsuda regarding article, "Plasminogen activator inhibitor-1 antagonist TM5441 attenuates Nω-nitro-L-arginine methyl ester-induced hypertension and vascular senescence". Circulation. 2014 Aug 26;130(9):e83. doi: 10.1161/CIRCULATIONAHA.113.007940. PubMed PMID: 25156921.

3: Bulbul T, Akosman MS, Yilmaz O, Ulutas E, Bulbul A. Supplementary dietary nitric oxide donor (sodium nitroprusside) or inhibitor (NG-nitro-L-arginine methyl ester) depressed growth performance and ovarian primordial and primary follicles in Japanese quail (Coturnix coturnix japonica) in a dose-dependent manner. Br Poult Sci. 2015;56(1):113-20. doi: 10.1080/00071668.2014.989489. Epub 2015 Jan 23. PubMed PMID: 25421145.

4: Shimizu M, Kochi T, Shirakami Y, Genovese S, Epifano F, Fiorito S, Mori T, Tanaka T, Moriwaki H. 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. Epub 2014 Jan 28. PubMed PMID: 24474144.

5: Wight JP, Haylor J, Muchaneta-Kubara EC, el Nahas AM. Differential effect of L-nitroarginine methyl ester on urinary cGMP and kidney growth in the conscious rat following uninephrectomy. Nephrol Dial Transplant. 1992;7(12):1185-9. PubMed PMID: 1337157.

6: Pollock DM, Polakowski JS, Opgenorth TJ, Pollock JS. Role of endothelin ET(A) receptors in the hypertension produced by 4-day L-nitroarginine methyl ester and cyclosporine treatment. Eur J Pharmacol. 1998 Apr 3;346(1):43-50. PubMed PMID: 9617750.

7: Chen TH, Liao FT, Yang YC, Wang JJ. Inhibition of inducible nitric oxide synthase ameliorates myocardial ischemia/reperfusion injury - induced acute renal injury. Transplant Proc. 2014 May;46(4):1123-6. doi: 10.1016/j.transproceed.2013.12.018. PubMed PMID: 24815143.

8: Yamaguchi T, Yamazaki T, Kawaguchi H, Tawa M, Nakamura Y, Shiota M, Osada-Oka M, Tanimoto A, Okamura T, Miura K, Iwao H, Yoshiyama M, Izumi Y. Noninvasive metabolic syndrome model using an extremely small minipig, the microminipig. J Pharmacol Sci. 2014;126(2):168-71. Epub 2014 Sep 19. PubMed PMID: 25242170.

9: Florian V, Caroline F, Francis C, Camille S, Fabielle A. Leptin modulates enteric neurotransmission in the rat proximal colon: an in vitro study. Regul Pept. 2013 Aug 10;185:73-8. doi: 10.1016/j.regpep.2013.06.010. Epub 2013 Jun 28. PubMed PMID: 23816465.

10: Nagashima R, Yamaguchi T, Tanaka H, Ogita K. Mechanism underlying the protective effect of tempol and Nω-nitro-L-arginine methyl ester on acoustic injury: possible involvement of c-Jun N-terminal kinase pathway and connexin26 in the cochlear spiral ligament. J Pharmacol Sci. 2010;114(1):50-62. Epub 2010 Aug 10. PubMed PMID: 20703012.

11: Nik Yusoff NS, Mustapha Z, Govindasamy C, Sirajudeen KN. Effect of Clonidine (an antihypertensive drug) treatment on oxidative stress markers in the heart of spontaneously hypertensive rats. Oxid Med Cell Longev. 2013;2013:927214. doi: 10.1155/2013/927214. Epub 2013 May 16. PubMed PMID: 23766863; PubMed Central PMCID: PMC3671561.

12: Peregud DI, Iakovleva AA, Stepanichev MIu, Panchenko LF, Guliaeva NV. [Role of NO/cGMP signaling cascade in the development of opium dependency]. Eksp Klin Farmakol. 2013;76(3):3-6. Russian. PubMed PMID: 23767094.

13: Ghasemi M, Karimollah AR, Bakhtiari B, Ghasemi A, Moezi L, Bahremand A, Ziaei P, Dehpour AR. Effect of biliary cirrhosis on neurogenic relaxation of rat gastric fundus and anococcygeus muscle: role of nitric oxide pathway. Dig Dis Sci. 2014 Nov;59(11):2675-81. doi: 10.1007/s10620-014-3225-0. Epub 2014 Jun 5. PubMed PMID: 24898099.

14: Avontuur JA, Buijk SL, Bruining HA. Distribution and metabolism of N(G)-nitro-L-arginine methyl ester in patients with septic shock. Eur J Clin Pharmacol. 1998 Oct;54(8):627-31. PubMed PMID: 9860150.

15: Kopincová J, Púzserová A, Bernátová I. L-NAME in the cardiovascular system - nitric oxide synthase activator? Pharmacol Rep. 2012;64(3):511-20. Review. PubMed PMID: 22814004.

16: Paulis L, Pechanova O, Zicha J, Krajcirovicova K, Barta A, Pelouch V, Adamcova M, Simko F. Melatonin prevents fibrosis but not hypertrophy development in the left ventricle of NG-nitro-L-arginine-methyl ester hypertensive rats. J Hypertens Suppl. 2009 Aug;27(6):S11-6. doi: 10.1097/01.hjh.0000358831.33558.97. PubMed PMID: 19633445.

17: Pfeiffer S, Leopold E, Schmidt K, Brunner F, Mayer B. Inhibition of nitric oxide synthesis by NG-nitro-L-arginine methyl ester (L-NAME): requirement for bioactivation to the free acid, NG-nitro-L-arginine. Br J Pharmacol. 1996 Jul;118(6):1433-40. PubMed PMID: 8832069; PubMed Central PMCID: PMC1909689.

18: Fujii N, McGinn R, Stapleton JM, Paull G, Meade RD, Kenny GP. Evidence for cyclooxygenase-dependent sweating in young males during intermittent exercise in the heat. J Physiol. 2014 Dec 1;592(23):5327-39. doi: 10.1113/jphysiol.2014.280651. Epub 2014 Oct 17. PubMed PMID: 25326453; PubMed Central PMCID: PMC4262342.

19: Serna E, Mauricio MD, Lluch P, Segarra G, Cortina B, Lluch S, Medina P. Basal release of nitric oxide in the mesenteric artery in portal hypertension and cirrhosis: role of dimethylarginine dimethylaminohydrolase. J Gastroenterol Hepatol. 2013 May;28(5):880-6. doi: 10.1111/jgh.12119. PubMed PMID: 23302093.

20: Lira VA. Exercise-induced cardioprotection: more to k‘NO’w. Cardiology. 2015;130(3):172-4. PubMed PMID: 25720747.