An internal standard for the quantification of metamizole
Related Products
Unlabeled Version(s)
15771Metamizole (sodium salt)
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Metamizole-d3 (sodium salt)

Item No. 26496

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl-d3)amino)methanesulfonate, monosodium salt
CAS Number
2512223-60-6
Synonyms
  • Dipyrone-d3
Molecular Formula
C13H13D3N3O4S • Na
Formula Weight
336.4
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
[O-]S(CN(C([2H])([2H])[2H])C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)(=O)=O.[Na+]
InChi Code
InChI=1S/C13H17N3O4S.Na/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11;/h4-8H,9H2,1-3H3,(H,18,19,20);/q;+1/p-1/i2D3;
InChi Key
DJGAAPFSPWAYTJ-MUTAZJQDSA-M
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    1 mg

    $401

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    Product Description

    Metamizole-d3 is intended for use as an internal standard for the quantification of metamizole (Item No. 15771) by GC- or LC-MS. Metamizole is a nonopioid prodrug that is rapidly hydrolyzed to the analgesic and antipyretic metabolites 4-methylaminoantipyrine (MAA) and 4-aminoantipyrine (AA).1 It inhibits COX-1 and COX-2 activity (IC50 = ~150 µg/ml for both in cell-free assays), as well as reduces increases in intracellular calcium levels induced by the TRPA1 agonist AITC in isolated rat and mouse dorsal root ganglia and IMR-90 human fibroblasts (IC50s = 30-91 µM in patch-clamp assays).2,3 Metamizole (6, 12, and 25 µg/ml) inhibits ADP- and epinephrine-induced platelet aggregation in human platelet-rich plasma (hPRP).4 It prevents fever induced by LPS, TNF-α, and IL-6, but not arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) or prostaglandin E2 (PGE2; Item No. 14010), in rats when administered at a dose of 120 mg/kg.5 Metamizole (250 and 500 mg/kg) increases the paw withdrawal threshold in the paw pressure test, indicating analgesic activity, in rat models of carrageenan-induced acute pain and postoperative incision pain.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rogosch, T., Sinning, C., Podlewski, A., et al. Novel bioactive metabolites of dipyrone (metamizol). Bioorg. Med. Chem. 20(1), 101-107 (2012).

    2. Campos, C., de Gregorio, R., García-Nieto, R., et al. Regulation of cyclooxygenase activity by metamizol. Eur. J. Pharmacol. 378(3), 339-347 (1999).

    3. Nassini, R., Fusi, C., Materazzi, S., et al. The TRPA1 channel mediates the analgesic action of dipyrone and pyrazolone derivatives. Br. J. Pharmacol. 172(13), 3397-3411 (2015).

    4. Papp, J., Sandor, B., Vamos, Z., et al. Antiplatelet effect of acetylsalicylic acid, metamizole and their combination - in vitro and in vivo comparisons. Clin. Hemorheol. Microcirc. 56(1), 1-12 (2014).

    5. De Souza, G.E.P., Cardoso, R.A., Melo, M.C.C., et al. A comparative study of the antipyretic effects of indomethacin and dipyrone in rats. Inflamm. Res. 51(1), 24-32 (2002).

    6. Ince, I., Aksoy, M., Ahiskalioglu, A., et al. A comparative investigation of the analgesic effects of metamizole and paracetamol in rats. J. Invest. Surg. 28(3), 173-180 (2015).