A derivative of acetaminophen
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Metacetamol

Item No. 33404

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(3-hydroxyphenyl)-acetamide
CAS Number
621-42-1
Synonyms
  • 3'-Hydroxyacetanilide
  • AMAP
  • N-acetyl-m-Aminophenol
  • N-acetyl-meta-Aminophenol
  • NSC 3990
Molecular Formula
C8H9NO2
Formula Weight
151.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.20 mg/mlEthanol: 5 mg/ml
λmax
246 nm
SMILES
O=C(C)NC1=CC(O)=CC=C1
InChi Code
InChI=1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10)
InChi Key
QLNWXBAGRTUKKI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 g

    $36

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    50 g

    $68

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    100 g

    $90

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    500 g

    $268

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    Product Description

    Metacetamol is a derivative of acetaminophen (Item No. 10024).1,2,3 Unlike acetaminophen, metacetamol is not cytotoxic to isolated mouse hepatocytes (LC50 = >10 mM).1 However, it does induce necrosis and depletion of glutathione (GSH) in isolated human hepatocytes when used at a concentration of 10 mM.2 Metacetamol (900 mg/kg) does not induce hepatic necrosis in mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Holme, J.A., Hongslo, J.K., Bjørge, C., et al. Comparative cytotoxic effects of acetaminophen (N-acetyl-p-aminophenol), a non-hepatotoxic regioisomer acetyl-m-aminophenol and their postulated reactive hydroquinone and quinone metabolites in monolayer cultures of mouse hepatocytes. Biochem. Pharmacol. 42(5), 1137-1142 (1991).

    2. Xie, Y., McGill, M.R., Du, K., et al. Mitochondrial protein adducts formation and mitochondrial dysfunction during N-acetyl-m-aminophenol (AMAP)-induced hepatotoxicity in primary human hepatocytes. Toxicol. Appl. Pharmacol. 289(2), 213-222 (2015).

    3. Nelson, E.B. The pharmacology and toxicology of meta-substituted acetanilide I: Acute toxicity of 3-hydroxyacetanilide in mice. Res. Commun. Chem. Pathol. Pharmacol. 28(3), 447-456 (1980).