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Merck
CN

109428

4-Hydroxyantipyrine

99%

Synonym(s):

4-Hydroxy-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one, NSC 174055

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
1672-63-5
Molecular Weight:
204.23
NACRES:
NA.22
PubChem Substance ID:
24846917
UNSPSC Code:
12352100
MDL number:
MFCD00003143
Assay:
99%

Key Documents

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InChI

1S/C11H12N2O2/c1-8-10(14)11(15)13(12(8)2)9-6-4-3-5-7-9/h3-7,14H,1-2H3

SMILES string

CN1N(c2ccccc2)C(=O)C(O)=C1C

InChI key

SKVPTPMWXJSBTF-UHFFFAOYSA-N

assay

99%

mp

184-186 °C (lit.)

functional group

ketone

Quality Level

200

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General description

4-Hydroxyantipyrine is formed during oxidative deamination of aminopyrine. It is a metabolite of antipyrine.

Application

4-Hydroxyantipyrine was used to study the relationships between the metabolism of antipyrine, hexobarbitone and theophylline in man. It was used in a study on flow injection analysis system for the characterisation of pharmaceutical compounds via combination of diode array UV, 1H NMR, FT-IR spectroscopy and time-of-flight mass spectrometry.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000281830
0000231851
0000219245
0000281830
0000231851

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Metabolism of drugs. LIX. A new metabolite of antipyrine.
H Yoshimura et al.
Biochemical pharmacology, 17(8), 1511-1516 (1968-08-01)
D Louden et al.
The Analyst, 125(5), 927-931 (2000-07-08)
A prototype flow injection analysis (FIA) system for the characterisation of compounds via a combination of diode array UV, 1H NMR, FT-IR spectroscopy and time-of-flight (TOF) mass spectrometry has been investigated using a number of pharmaceuticals and related compounds as
The effect of cimetidine on antipyrine metabolism in calves.
K Janus et al.
Journal of veterinary pharmacology and therapeutics, 20(1), 73-76 (1997-02-01)
K Janus et al.
Research in veterinary science, 60(3), 234-237 (1996-05-01)
Single doses of 15 mg kg-1 antipyrine were given intravenously to 10 female calves of the black and white breed at one, two, four, six, eight and 12 weeks of age, and the concentrations of antipyrine, 4-hydroxyantipyrine (4-OHA), 3-hydroxymethyl-antipyrine (HMA)
J E Sharer et al.
Drug metabolism and disposition: the biological fate of chemicals, 24(4), 487-494 (1996-04-01)
Antipyrine biotransformation has been used extensively in clinical studies as a marker for general hepatic oxidative or cytochrome P450 (P450)-mediated, metabolism. Studies have indicated that more than one P450 is involved in the formation of the three major human metabolites
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