A derivative of acetaminophen
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N-acetyl-2-Aminophenol

Item No. 35829

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyphenyl)-acetamide
CAS Number
614-80-2
Synonyms
  • AAP
  • 2-Acetamidophenol
  • 2-Acetaminophenol
  • N-acetyl-o-Aminophenol
  • N-acetyl-ortho-Aminophenol
  • NSC 3989
  • Orthocetamol
Molecular Formula
C8H9NO2
Formula Weight
151.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMSO: 11 mg/mlEthanol: Slightly solublePBS (pH 7.2): 0.3 mg/ml
λmax
243 nm
SMILES
O=C(C)NC1=C(O)C=CC=C1
InChi Code
InChI=1S/C8H9NO2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11H,1H3,(H,9,10)
InChi Key
ADVGKWPZRIDURE-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    N-acetyl-2-Aminophenol is a derivative of the analgesic and antipyretic acetaminophen (Item No. 10024) that has been found in P. fluorescens.1,2 It inhibits platelet aggregation induced by ADP (Item Nos. 16778 | 21121) or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in isolated human platelet-rich plasma when used at a concentration of 50 µM.1 N-acetyl-2-Aminophenol (1 mg/kg) decreases disease severity and prevents increases in paw volume in a rat model of collagen-induced arthritis. It has been used as a synthetic intermediate in the synthesis of compounds with antimalarial activity.3 N-acetyl-2-Aminophenol is also a potential impurity in commercial preparations of acetaminophen.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Qureshı, Z., Aslam, M., Saeed, T., et al. Anti-platelet and anti-arthritic Activity of orthocetamol (2-acetamıdophenol): An ortho (O) positional isomer of paracetamol. Turk. J. Pharm. Sci. 12(3), 75-94 (2015).

    2. Slininger, P.J., Burkhead, K.D., Schisler, D.A., et al. Isolation, identification, and accumulation of 2-acetamidophenol in liquid cultures of the wheat take-all biocontrol agent Pseudomonas fluorescens 2-79. Appl. Microbiol. Biotechnol. 54(3), 376-381 (2000).

    3. Dziwornu, G.A., Coertzen, D., Leshabane, M., et al. Incorporating phenolic mannich base side chains inhibit microtubule and hemozoin formation: Structure-activity relationship and in vivo oral efficacy studies. J. Med. Chem. 64(8), 5198-5215 (2021).

    4. Arıkan, C.C., Kulabaş, N., and Küçükgüzel, I. Synthesis and standardization of an impurity of acetaminophen, development and validation of liquid chromatographic method. J. Pharm. Biomed. Anal. 223, 115123 (2023).