A less active enantiomer of the NO synthase inhibitor L-NAME
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D-NAME (hydrochloride)

Item No. 21687

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N5-[imino(nitroamino)methyl]-D-ornithine, methyl ester, monohydrochloride
CAS Number
50912-92-0
Synonyms
  • D-NG-Nitroarginine methyl ester
  • N(G)-Nitro-D-Arginine methyl ester
Molecular Formula
C7H15N5O4 • HCl
Formula Weight
269.7
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
210, 269 nm
SMILES
[H]N(/C(N([H])CCC[C@@H](N)C(OC)=O)=N/[H])[N+]([O-])=O.Cl
InChi Code
InChI=1S/C7H15N5O4.ClH/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);1H
InChi Key
QBNXAGZYLSRPJK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $35

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    500 mg

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    1 g

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    5 g

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    Product Description

    N(G)-Nitro-D-arginine methyl ester (D-NAME) is the less active enantiomer of the nitric oxide (NO) synthase inhibitor N(G)-nitro-L-arginine methyl ester (L-NAME; Item No. 80210). D-NAME was initially thought to be inactive and was often used as a negative control for L-NAME.1,2 Later studies showed that D-NAME (40 mg/kg/day in rats) can have similar but less pronounced effects as L-NAME (40 mg/kg/day in rats) in the cardiovascular system, particularly at long-term timepoints.3 D-NAME (3-10 µg/mouse) had no effect on nociception in mice assessed using the tail flick test.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Palmer, R.M.J., Rees, D.D., Ashton, D.S., et al. L-arginine is the physiological precursor for the formation of nitric oxide in endothelium-dependent relaxation. Biochem. Biophys. Res. Commun. 153(3), 1251-1256 (1988).

    2. Chinellato, A., Froldi, G., Caparrota, L., et al. Pharmacological characterization of endothelial cell nitric oxide synthase inhibitors in isolated rabbit aorta. Life Sci. 62(6), 479-490 (1998).

    3. Babál, P., Pechánová, O., and Bernátová, I. Long-term administration of D-NAME induces hemodynamic and structural changes in the cardiovascular system. Physiol. Res. 49(1), 47-54 (2000).

    4. Kawabata, A., Umeda, N., and Takagaki, H. L-arginine exerts a dual role in nociceptive processing in the brain: Involvement of the kyotorphin-Met-enkephalin pathway and NO-cyclic GMP pathway. Br. J. Pharmacol. 109(1), 73-79 (1993).

    Product Citations

    Jarazo Dietrich, S., Fass, M.I., Jacobo, P.V., et al. Inhibition of NOS-NO system prevents autoimmune orchitis development in rats: Relevance of NO released by testicular macrophages in germ cell apoptosis and testosterone secretion. PLoS One 10(6), e0128709 (2015).