L-NMMA acetate | CAS#53308-83-1 | relaxing factor inhibitor

MedKoo Cat#: 563500 | Name: L-NMMA acetate

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Description:

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

L-NMMA acetate is an endothelium-derived relaxing factor inhibitor. It acts by inhibiting the generation of NO from arginine.

Chemical Structure

L-NMMA acetate

CAS#53308-83-1

Theoretical Analysis

MedKoo Cat#: 563500

Name: L-NMMA acetate

CAS#: 53308-83-1

Chemical Formula: C9H20N4O4

Exact Mass: 248.1485

Molecular Weight: 248.28

Elemental Analysis: C, 43.54; H, 8.12; N, 22.57; O, 25.78

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 315.00	2 Weeks
100mg	USD 550.00	2 Weeks

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Synonym

L-NMMA acetate; L NMMA acetate; LNMMA acetate; ANO-1020; ANO 1020; ANO1020; Tilarginine acetate; NG-Monomethyl-L-arginine acetate;

IUPAC/Chemical Name

(E)-Nw'-methyl-L-arginine compound with acetic acid (1:1)

InChi Key

IKPNWIGTWUZCKM-JEDNCBNOSA-N

InChi Code

InChI=1S/C7H16N4O2.C2H4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13;1-2(3)4/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);1H3,(H,3,4)/t5-;/m0./s1

SMILES Code

O=C(O)[C@@H](N)CCCN/C(N)=N/C.CC(O)=O

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-NMMA acetate is a nitric oxide synthase inhibitor of all NOS isoforms including NOS1, NOS2, and NOS3.

In vitro activity:

Consistent with previous reports (Olken, N. M., et al., Biochem. Biophys. Res. Commun. 177, 828-833, 1991), NMMA was a mechanism-based irreversible inhibitor of iNOS, exhibiting time- and concentration-dependent inactivation of iNOS with a KI equal to 2.6 microM and a kinact equal to 0.042 min-1. When assayed without a preincubation period, NMMA exhibited typical reversible inhibition of iNOS (Ki = 3.9 microM). NMMA also reversibly inhibited nNOS and the eNOS with Ki equal to 0.65 and 0.7 microM, respectively. Reference: Arch Biochem Biophys. 1995 Jun 20;320(1):170-6. https://pubmed.ncbi.nlm.nih.gov/7540822/

In vivo activity:

The authors investigated the effect of NG-monomethyl-L-arginine acetate (L-NMMA), a nitric oxide synthase (NOS) inhibitor, on the contractile function of skeletal muscle following ischemia/reperfusion (I/R) injury. The extensor digitorum longus (EDL) muscles of 50 rats were divided into seven groups. Following L-NMMA administration at three different dosages, contractile function of I/R muscle decreased in a dose-dependent manner. The highest dosage of L-NMMA (10 micromol/min) reduced the average maximal twitch force to 15 percent and the isometric tetanic contractile forces to between 10 to 23 percent. Reference: J Reconstr Microsurg. 1999 Jan;15(1):55-60. https://pubmed.ncbi.nlm.nih.gov/10025531/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.3	1.01
	Ethanol	1.0	4.03
	PBS (pH 7.2)	10.0	40.28
	Water	37.5	150.92

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 248.28 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

Formulation protocol:

1. Xia Y, Li Y, Khalid W, Bikson M, Fu BM. Direct Current Stimulation Disrupts Endothelial Glycocalyx and Tight Junctions of the Blood-Brain Barrier in vitro. Front Cell Dev Biol. 2021 Sep 28;9:731028. doi: 10.3389/fcell.2021.731028. PMID: 34650977; PMCID: PMC8505730. 2. Reif DW, McCreedy SA. N-nitro-L-arginine and N-monomethyl-L-arginine exhibit a different pattern of inactivation toward the three nitric oxide synthases. Arch Biochem Biophys. 1995 Jun 20;320(1):170-6. doi: 10.1006/abbi.1995.1356. PMID: 7540822. 3. Joneschild ES, Chen LE, Seaber AV, Frankel ES, Urbaniak JR. Effect of a NOS inhibitor, L-NMMA, on the contractile function of reperfused skeletal muscle. J Reconstr Microsurg. 1999 Jan;15(1):55-60. doi: 10.1055/s-2007-1000071. PMID: 10025531. 4. Nakamura T, Prewitt RL. Effect of NG-monomethyl-L-arginine on arcade arterioles of rat spinotrapezius muscles. Am J Physiol. 1991 Jul;261(1 Pt 2):H46-52. doi: 10.1152/ajpheart.1991.261.1.H46. PMID: 1858929.

In vitro protocol:

In vivo protocol:

1. Joneschild ES, Chen LE, Seaber AV, Frankel ES, Urbaniak JR. Effect of a NOS inhibitor, L-NMMA, on the contractile function of reperfused skeletal muscle. J Reconstr Microsurg. 1999 Jan;15(1):55-60. doi: 10.1055/s-2007-1000071. PMID: 10025531. 2. Nakamura T, Prewitt RL. Effect of NG-monomethyl-L-arginine on arcade arterioles of rat spinotrapezius muscles. Am J Physiol. 1991 Jul;261(1 Pt 2):H46-52. doi: 10.1152/ajpheart.1991.261.1.H46. PMID: 1858929.

1: Halliday GM, Byrne SN, Kuchel JM, Poon TS, Barnetson RS. The suppression of immunity by ultraviolet radiation: UVA, nitric oxide and DNA damage. Photochem Photobiol Sci. 2004 Aug;3(8):736-40. Epub 2004 Feb 3. Review. PubMed PMID: 15295628. 2: Satoh H, Nishida S. Electropharmacological actions of Ginkgo biloba extract on vascular smooth and heart muscles. Clin Chim Acta. 2004 Apr;342(1-2):13-22. Review. PubMed PMID: 15026263. 3: Yamashita M. [Analysis of the mechanism for the anti-inflammatory effect of the anti-rheumatic drug auranofin]. Yakugaku Zasshi. 2000 Mar;120(3):265-74. Review. Japanese. PubMed PMID: 10723268. 4: Colton CA, Snell J, Chernyshev O, Gilbert DL. Induction of superoxide anion and nitric oxide production in cultured microglia. Ann N Y Acad Sci. 1994 Nov 17;738:54-63. Review. PubMed PMID: 7530427.