D-NAME | 141968-19-6 | NO synthetase inhibitor

MedKoo Cat#: 140101 | Name: D-NAME

Description:

WARNING: This product is for research use only, not for human or veterinary use.

An enantiomer of L-NAME, D-NAME is a weak nitric oxide synthetase inhibitor.

Chemical Structure

D-NAME

CAS#141968-19-6

Theoretical Analysis

MedKoo Cat#: 140101

Name: D-NAME

CAS#: 141968-19-6

Chemical Formula: C8H16N4O4

Exact Mass: 232.1172

Molecular Weight: 232.24

Elemental Analysis: C, 41.37; H, 6.94; N, 24.13; O, 27.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

51298-62-5

Synonym

L-NAME

IUPAC/Chemical Name

methyl (R,E)-2-amino-5-((amino(carboxyamino)methylene)amino)pentanoate

InChi Key

WSXMVRLABAVBQK-RXMQYKEDSA-N

InChi Code

InChI=1S/C8H16N4O4/c1-16-6(13)5(9)3-2-4-11-7(10)12-8(14)15/h5H,2-4,9H2,1H3,(H,14,15)(H3,10,11,12)/t5-/m1/s1

SMILES Code

COC([C@H](N([H])[H])CCC/N=C(N(C(O)=O)[H])\N([H])[H])=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

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

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 232.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Babál P, Pechánová O, Bernátová I. Long-term administration of D-NAME induces hemodynamic and structural changes in the cardiovascular system. Physiol Res. 2000;49(1):47-54. PMID: 10805404. 2: Liu T, Zhang M, Mukosera GT, Borchardt D, Li Q, Tipple TE, Ishtiaq Ahmed AS, Power GG, Blood AB. L-NAME releases nitric oxide and potentiates subsequent nitroglycerin-mediated vasodilation. Redox Biol. 2019 Sep;26:101238. doi: 10.1016/j.redox.2019.101238. Epub 2019 Jun 4. PMID: 31200239; PMCID: PMC6565607. 3: Halkar RK, Aarsvold JN. Intraoperative probes. J Nucl Med Technol. 1999 Sep;27(3):188-93; quiz 195-6. PMID: 10512473. 4: Pechánová O, Bernátová I, Babál P. Structural alterations in the heart after long-term L-NAME and D-NAME treatment. Gen Physiol Biophys. 1999 Dec;18 Suppl 1:6-9. PMID: 10707823. 5: Duarte ID, Ferreira SH. L-NAME causes antinociception by stimulation of the arginine-NO-cGMP pathway. Mediators Inflamm. 2000;9(1):25-30. doi: 10.1080/09629350050024348. PMID: 10877451; PMCID: PMC1781740. 6: Das R, Kravtsov GM, Ballard HJ, Kwan CY. L-NAME inhibits Mg(2+)-induced rat aortic relaxation in the absence of endothelium. Br J Pharmacol. 1999 Sep;128(2):493-9. doi: 10.1038/sj.bjp.0702737. PMID: 10510463; PMCID: PMC1571625. 7: Káldi I, Dittmar M, Pierce P, Anderson RE. L-NAME protects against acute light damage in albino rats, but not against retinal degeneration in P23H and S334ter transgenic rats. Exp Eye Res. 2003 Apr;76(4):453-61. doi: 10.1016/s0014-4835(02)00334-2. PMID: 12634110. 8: Cui S, Shibamoto T, Liu W, Takano H, Zhao ZS, Kurata Y. Effects of Hct on L-NAME-induced potentiation of anaphylactic presinusoidal constriction in perfused rat livers. J Cardiovasc Pharmacol. 2006 Jul;48(1):827-33. doi: 10.1097/01.fjc.0000232063.87708.29. PMID: 16891911. 9: Seckler JM, Grossfield A, May WJ, Getsy PM, Lewis SJ. Nitrosyl factors play a vital role in the ventilatory depressant effects of fentanyl in unanesthetized rats. Biomed Pharmacother. 2022 Feb;146:112571. doi: 10.1016/j.biopha.2021.112571. Epub 2021 Dec 22. PMID: 34953397; PMCID: PMC8776621. 10: Shibamoto T, Ruan Z, Cui S, Liu W, Zhao ZS, Takano H, Kurata Y, Koizumi T, Kubo K. The sinusoidal pressure during ischemia-reperfusion injury in perfused mouse liver pretreated with or without L-NAME. J Surg Res. 2007 May 1;139(1):30-5. doi: 10.1016/j.jss.2006.07.052. Epub 2007 Feb 9. PMID: 17292416. 11: Wayman CP, Pike NV, Wilson JF. N-methyl-D-aspartate (NMDA) stimulates release of alpha-MSH from the rat hypothalamus through release of nitric oxide. Brain Res. 1994 Dec 15;666(2):201-6. doi: 10.1016/0006-8993(94)90773-0. PMID: 7882030. 12: Turner CH, Takano Y, Owan I, Murrell GA. Nitric oxide inhibitor L-NAME suppresses mechanically induced bone formation in rats. Am J Physiol. 1996 Apr;270(4 Pt 1):E634-9. doi: 10.1152/ajpendo.1996.270.4.E634. PMID: 8928770. 13: Rehman A, Whiteman M, Halliwell B. Scavenging of hydroxyl radicals but not of peroxynitrite by inhibitors and substrates of nitric oxide synthases. Br J Pharmacol. 1997 Dec;122(8):1702-6. doi: 10.1038/sj.bjp.0701556. PMID: 9422817; PMCID: PMC1565113. 14: Shimada K, Uzui H, Ueda T, Lee JD, Kishimoto C. N-Acetylcysteine Ameliorates Experimental Autoimmune Myocarditis in Rats via Nitric Oxide. J Cardiovasc Pharmacol Ther. 2015 Mar;20(2):203-10. doi: 10.1177/1074248414547574. Epub 2014 Aug 20. PMID: 25147347. 15: Sugimoto Y, Yamada J, Yoshikawa T, Horisaka K. Inhibitory effects of a nitric oxide synthase inhibitor, N(G)-nitro-L-arginine methyl ester (L-NAME), on 2-deoxy-D-glucose-induced hyperglycemia in rats. Biol Pharm Bull. 1997 Dec;20(12):1307-9. doi: 10.1248/bpb.20.1307. PMID: 9448110. 16: Teixeira MM, Williams TJ, Hellewell PG. Role of prostaglandins and nitric oxide in acute inflammatory reactions in guinea-pig skin. Br J Pharmacol. 1993 Dec;110(4):1515-21. doi: 10.1111/j.1476-5381.1993.tb13994.x. PMID: 8306095; PMCID: PMC2175893. 17: Moreno Júnior H, Nathan LP, Metze K, Costa SK, Antunes E, Hyslop S, Zatz R, de Nucci G. Non-specific inhibitors of nitric oxide synthase cause myocardial necrosis in the rat. Clin Exp Pharmacol Physiol. 1997 May;24(5):349-52. doi: 10.1111/j.1440-1681.1997.tb01200.x. PMID: 9143786. 18: Souza HC, Ballejo G, Salgado MC, Da Silva VJ, Salgado HC. Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats. Am J Physiol Heart Circ Physiol. 2001 Feb;280(2):H844-50. doi: 10.1152/ajpheart.2001.280.2.H844. PMID: 11158985. 19: Hogaboam CM, Collins SM, Blennerhassett MG. Effects of oral L-NAME during Trichinella spiralis infection in rats. Am J Physiol. 1996 Aug;271(2 Pt 1):G338-46. doi: 10.1152/ajpgi.1996.271.2.G338. PMID: 8770050. 20: Tsai WC, Strieter RM, Zisman DA, Wilkowski JM, Bucknell KA, Chen GH, Standiford TJ. Nitric oxide is required for effective innate immunity against Klebsiella pneumoniae. Infect Immun. 1997 May;65(5):1870-5. doi: 10.1128/iai.65.5.1870-1875.1997. PMID: 9125574; PMCID: PMC175233.