Name | (2S)-5-{[(E)-amino(methyliminio)methyl]amino}-2-ammoniopentanoate |
Synonyms | Nα-Methyl-L-arginine N-Monomethyl-L-arginine Ngamma-methyl-L-arginine acetate NG-Monomethyl-L-arginine acetate salt L-NG-Monomethylarginine, Acetate Salt (L-NMMA) (2S)-5-{[(E)-amino(methyliminio)methyl]amino}-2-ammoniopentanoate L-NMMA, NG-Monomethyl-L-arginine acetate salt, Nω-Methyl-L-arginine acetate salt, N5-(Methylamidino)-L-ornithine acetate salt |
CAS | 53308-83-1 |
InChI | InChI=1/C7H16N4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11)/p+1/t5-/m0/s1 |
InChIKey | IKPNWIGTWUZCKM-JEDNCBNOSA-N |
Molecular Formula | C9H20N4O4 |
Molar Mass | 248.28 |
Density | 1.2162 (rough estimate) |
Melting Point | 180-190 °C |
Boling Point | 391.35°C (rough estimate) |
Specific Rotation(α) | D22 +9.5° (c = 0.10 in water) |
Flash Point | 191.3°C |
Solubility | H2O: 1mg/mL, clear, colorless |
Vapor Presure | 2.92E-07mmHg at 25°C |
Appearance | Powder |
Color | White to Off-white |
BRN | 6674255 |
Storage Condition | 2-8°C |
Stability | Store at - 5°C; Desiccate Recommended |
Refractive Index | 1.6300 (estimate) |
In vitro study | L-NMMA, starting from 100 μM, produces a concentration-dependent inhibition of the evoked relaxations (2Hz); maximal inhibition at 1 mM averaged about 35%. The inhibitory effect of L-NMMA is unchanged by previous incubation with D-arginine while it is prevented by L-arginine (L-Arg). L-NMMA does not affect isoprenaline-induced relaxation. Superfusion of L-NMMA reduces arteriolar diameter and causes dose-dependent increases in arteriolar tone. The onset of action of L-NMMA is nearly immediate. L-NMMA inhibits vasodilator responses to the endothelium-dependent vasodilator ACh but not to the endothelium-independent NP. NE induced dose-related vasoconstriction that is significantly potentiated by L-NMMA. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
HS Code | 29252900 |
Biological activity | L-NMMA acetate is an inhibitor of nitric oxide synthase, which inhibits all subtypes of nitric oxide synthase NOS1,NOS2 and NOS3. Ki values for nNOS (rat), eNOS (human), and iNOS (mouse) were 0.18,0.4,6 µM, respectively. |
target | Ki: 0.18 µM (nNOS), 0.4 µM (eNOS), 6 µM (iNOS) |