An active metabolite of metamizole
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Pro-drug Form(s)
15771Metamizole (sodium salt)
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4-Methylaminoantipyrine (hydrochloride)

Item No. 31612

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2-dihydro-1,5-dimethyl-4-(methylamino)-2-phenyl-3H-pyrazol-3-one, monohydrochloride
CAS Number
856307-27-2
Synonyms
  • Metamizole Impurity C
Molecular Formula
C12H15N3O • HCl
Formula Weight
253.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O=C1N(C2=CC=CC=C2)N(C)C(C)=C1NC.Cl
InChi Code
InChI=1S/C12H15N3O.ClH/c1-9-11(13-2)12(16)15(14(9)3)10-7-5-4-6-8-10;/h4-8,13H,1-3H3;1H
InChi Key
NNONRTWOIVTAHL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $219

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    Product Description

    4-Methylaminoantipyrine is a major active metabolite of the non-opioid prodrug metamizole (Item No. 15771).1 It is formed from metamizole by non-enzymatic hydrolysis in the gastrointestinal tract.2 4-Methylaminoantipyrine (0.1 mM) inhibits production of prostaglandin E2 (PGE2; Item No. 14010) induced by the calcium ionophore A23187 (Item Nos. 11016 | 22030) in isolated mouse peritoneal macrophages.3 It increases the paw withdrawal threshold in a rat model of carrageenan-induced hyperalgesia when administered at a dose of 160 µg/paw.4 4-Methylaminoantipyrine (60, 90, and 120 mg/kg) reduces LPS-induced pyrexia in rats.5 It is also a potential impurity found in commercial preparations of metamizole.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. Nikolova, I., Tencheva, J., Voynikov, Y., et al. Metamizole: A review profile of a well-known “forgotten” drug. Part I: Pharmaceutical and nonclinical profile. Biotechnol. Biotechnol. Equip. 26(6), 3329-3337 (2012).

    3. Brune, K., Aehringhaus, U., and Peskar, B.A. Pharmacological control of leukotriene and prostaglandin production from mouse peritoneal macrophages. Agents Actions 14(5-6), 729-734 (1984).

    4. Gonçalves Dos Santos, G., Vieira, W.F., Vendramini, P.H., et al. Dipyrone is locally hydrolyzed to 4-methylaminoantipyrine and its antihyperalgesic effect depends on CB2 and κ-opioid receptors activation. Eur. J. Pharmacol. 874, 173005 (2020).

    5. Malvar, D.d.C., Aguiar, F.A., Vaz Ade, L., et al. Dipyrone metabolite 4-MAA induces hypothermia and inhibits PGE2 -dependent and -independent fever while 4-AA only blocks PGE2 -dependent fever. Br. J. Pharmacol. 171(15), 3666-3679 (2014).

    6. Vieira, J.C., Sversut, R.A., Maciel, I.T., et al. HPLC–DAD method for simultaneous determination of dipyrone (metamizole) and caffeine in tablets and identification of major degradation product by direct infusion ESI–MS. Chromatographia 80(3), 489–495 (2017).