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A7205

Sigma-Aldrich

3-Acetamidophenol

97%

Synonym(s):

3′-Hydroxyacetanilide

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About This Item

Linear Formula:
CH3CONHC6H4OH
CAS Number:
621-42-1
Molecular Weight:
151.16
Beilstein:
907998
EC Number:
210-687-0
MDL number:
MFCD00002263
UNSPSC Code:
12352100
PubChem Substance ID:
24891188
NACRES:
NA.22

Assay

97%

form

crystals

mp

145-148 °C (lit.)

SMILES string

CC(=O)Nc1cccc(O)c1

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

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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M A Tirmenstein et al.
The Journal of biological chemistry, 265(6), 3059-3065 (1990-02-25)
The administration of a hepatotoxic dose of acetaminophen (250 mg/kg) to mice induced the loss of protein thiols in mouse liver. Our data suggest that a significant portion of this loss was due to protein thiol oxidation. The administration of
J A Holme et al.
Biochemical pharmacology, 42(5), 1137-1142 (1991-08-08)
Toxic effects of acetaminophen (paracetamol, N-acetyl-p-aminophenol, APAP) in monolayer cultures of mouse hepatocytes developed over a period of 18 hr. N-Acetyl-m-aminophenol (AMAP) was approximately 10-fold less toxic than APAP, despite the fact that it bound covalently to a greater extent
A M Matthews et al.
Toxicology letters, 90(1), 77-82 (1997-01-15)
The hepatotoxicity of the analgesic acetaminophen has been previously attributed to metabolic activation by cytochrome P450 to the reactive intermediate N-acetyl-p-benzoquinone imine. At therapeutic doses this species is detoxified by reaction with glutathione; however, following a hepatotoxic dose, liver glutathione
M S Rashed et al.
Drug metabolism and disposition: the biological fate of chemicals, 18(5), 765-770 (1990-09-01)
The metabolism and disposition of acetaminophen (APAP) and a non-hepatotoxic regioisomer, 3'-hydroxyacetanilide (AMAP), were investigated in the mouse using 14C-labeled analogues. Covalent binding of metabolites of both compounds was observed on the order of 1 nmol/mg tissue protein. AMAP binding
Lydia M Kwast et al.
Toxicological sciences : an official journal of the Society of Toxicology, 121(2), 312-319 (2011-03-16)
Immune-mediated drug hypersensitivity reactions are important causes of black box warnings and drug withdrawals. Despite the high demand for preclinical screening tools, no validated in vitro or in vivo models are available. In the current study, we used a previously
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