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109428

Sigma-Aldrich

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
MDL number:
MFCD00003143
UNSPSC Code:
12352100
PubChem Substance ID:
24846917
NACRES:
NA.22

Assay

99%

mp

184-186 °C (lit.)

SMILES string

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

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

InChI key

SKVPTPMWXJSBTF-UHFFFAOYSA-N

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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pharmacokinetics of antipyrine in calves after intravenous and oral administration.
K Janus et al.
Journal of veterinary pharmacology and therapeutics, 19(5), 408-410 (1996-10-01)
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
Metabolism of drugs. LIX. A new metabolite of antipyrine.
H Yoshimura et al.
Biochemical pharmacology, 17(8), 1511-1516 (1968-08-01)
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)
H A Ali et al.
Human & experimental toxicology, 13(10), 658-662 (1994-10-01)
1. We measured the antipyrine clearance in 18 healthy Saudi subjects and determined the urinary excretion of three of its metabolites: 4-hydroxyantipyrine (4-OH AP), norantipyrine (NOR AP) and 3 hydroxymethylantipyrine (3-OHM AP) in 21 subjects. 2. The mean +/- SD
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