ChemicalBook > CAS DataBase List > Antipyrine

Antipyrine

Product Name
Antipyrine
CAS No.
60-80-0
Chemical Name
Antipyrine
Synonyms
PHENAZONE;Antipyrin;Antipirin;Fenazone;Phenozone;ANALGESINE;ANTIPYRENE;Antypirine;2,3-DIMETHYL-1-PHENYL-5-PYRAZOLONE;1,5-Dimethyl-2-phenylpyrazol-3-one
CBNumber
CB8200943
Molecular Formula
C11H12N2O
Formula Weight
188.23
MOL File
60-80-0.mol
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Antipyrine Property

Melting point:
109-111 °C(lit.)
Boiling point:
319 °C
Density 
1,19 g/cm3
refractive index 
1.5850 (estimate)
storage temp. 
2-8°C
solubility 
H2O: soluble1 gm in less than 1ml
form 
Crystalline Powder
pka
pKa 1.4 (Uncertain)
color 
White
biological source
rabbit
Water Solubility 
1000 g/L (20 ºC)
Merck 
14,716
BRN 
157775
Stability:
Stable. Incompatible with ammonia, strong acids, alkalies, strong oxidizing agents, metallic salts, phenol.
LogP
0.380
CAS DataBase Reference
60-80-0(CAS DataBase Reference)
NIST Chemistry Reference
Antipyrine(60-80-0)
EPA Substance Registry System
Antipyrine (60-80-0)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36-37/39
RIDADR 
3249
WGK Germany 
1
RTECS 
CD2450000
F 
10
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29331190
Toxicity
LD50 orally in rats: 1.8 g/kg (Hart)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2347
Product name
Antipyrine
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500MG
Price
$216
Updated
2025/07/31
Sigma-Aldrich
Product number
P0800000
Product name
Phenazone
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
20 mg
Price
$225
Updated
2025/07/31
Sigma-Aldrich
Product number
ABF1169
Product name
Anti-Pyrin
Purity
from rabbit, purified by affinity chromatography
Packaging
25μL
Price
$182
Updated
2025/07/31
Sigma-Aldrich
Product number
ABF1169
Product name
Anti-Pyrin
Purity
from rabbit, purified by affinity chromatography
Packaging
100μL
Price
$429
Updated
2025/07/31
Sigma-Aldrich
Product number
1040005
Product name
Antipyrine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$376
Updated
2025/07/31
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Antipyrine Chemical Properties,Usage,Production

Chemical Properties

Colorless crystal or white crystalline powder. Soluble in benzene, ethanol, water, chloroform, slightly soluble in ether. Odorless, slightly bitter.

History

Antipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.

Uses

Antipyrine has been used for immunoblotting. It has also been used as an internal reference marker for studying the transport characteristics of platinum-containing drug, cisplatin in the human placenta in vitro. Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

Definition

ChEBI: Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic and an environmental contaminant.

Preparation

Antipyrine (1) was prepared from the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with methyl iodide in methanol or in acetonitrile containing sodium bicarbonate in water in 58% yield. The reaction of 1-methyl-2-phenylhydrazine (2) with methyl 3-oxobutanoate (3) in acetonitrile gave 1 and pyrazolone 4 . Krohn has been reported the synthesis of 1 from the reaction of 5 with dimethyl sulfate in 71% yield. The reaction of pyrazolone 6 with methanol in the presence of triphenylphosphine afforded 1 (14%) and pyrazole 7 (53%). The same reaction was reported by Pegurier et al by heating the reactants in methanol containing calcium monoxide. Knorr early reported also, the synthesis of antipyrine from heating of 1-phenyl-5-ethoxy-3- methylpyrazole (8) with methyl iodide in methanol.

brand name

Aerol;Antigestin;Asthma dellipsoids;Aurafair;Auralgicin;Auraltone;Bajumol;Breezeazy;Calmasmin;Cetussan;Codalgin;Crema antisolar evanescente;Doleron novum;Dolo-med-much;Dol-stop;Kalopsis;Lanceotic;Lavylgan;Mig-antos;Migranin;Natt-lunedon;Neo-felsol;Orecil;Otipyrin;Otosan-sulfan;Otothricinol;Palacaine;Pasta antisola;Pomada heridas;Prednefrin;Prefrin liquifilm;Prefrin z;Priatan;Prophyllen;Remolmed;Salicopil;Sedaural;Sedonan;Shhe 21;Spalt n;Tympagesic;Visublefarite.

World Health Organization (WHO)

Phenazone is a pyrazolone derivative chemically related to aminophenazone. Some regulatory authorities have imposed restrictions on its use on these grounds. However, a recent international study showed no statisticallybased evidence of an association with agranulocytosis or aplastic anaemia. Nor does it share with aminophenazone the propensity to produce potentially carcinogenic nitrosamines.

General Description

Antipyrine is an antipyretic agent used for the symptomatic treatment of acute otitis media, most commonly in combination with benzocaine. One of the earliest widely used analgesics and antipyretics, antipyrine was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.

Biochem/physiol Actions

Antipyrine also referred to as phenazone or phenazonum is an anti-inflammatory agent that possesses analgesic, antipyretic and platelet-inhibitory actions.

Safety Profile

A human Doison bv 1 i an unspecified route. Moderately toxic via ingestion, subcutaneous, and intravenous routes. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Antipyrine crystallises from EtOH/water mixture, *benzene, *benzene/pet ether or hot water (charcoal), and the crystals are dried under a vacuum. [Beilstein 24 H 27, 24 III/IV 75.]

Antipyrine Preparation Products And Raw materials

Raw materials

Ethyl acetoacetate Methanol solution 3-Methylpyrazole Methylpyridone Pyrazolone Methylhydrazine Methyl bromide Dimethyl sulfate

Preparation Products

4-Aminoantipyrine
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View Lastest Price from Antipyrine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Antipyrine 60-80-0
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
5ton/month
Release date
2025-07-31
Hebei Chuanghai Biotechnology Co., Ltd
Product
Antipyrine/Phenazone/Analgesine 60-80-0
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-04
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Antipyrine 60-80-0
Price
US $150.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500kg
Release date
2024-12-24

60-80-0, AntipyrineRelated Search:

ETHANE Dimethyl sulfoxide Dimethyl ether Dimethyl sulfate Dimethyl carbonate Sildenafil citrate Dimethyl fumarate 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Phenacetin Dacthal Finasteride Chlorodimethylphenylsilane Dihydromyrcenol Cefazolin Cefazolin sodium salt N,N-Dimethylformamide Dimethyl sebacate Dimethyl sulfide

  • 1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-on
  • 1,5-Dimethyl1-2-phenyl-3-pyrazolone
  • phenazone(pharmaceutical)
  • Phenozone
  • Phenyldimethyl isopropyl pyrazolone
  • Phenylon
  • Phenylone
  • Pyrazophyl
  • Sedatin
  • Sedatine
  • OXYDIMETHYLQUINIZINE
  • PHENAZONUM
  • PHENAZONE
  • ANALGESINE
  • 1,5-DIMETHYL-2-PHENYL-3-PYRAZOLONE
  • 1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
  • 2,3-DIMETHYL-1-PHENYL-3-PYRAZOLIN-5-ONE
  • 2,3-DIMETHYL-1-PHENYL-5-PYRAZOLONE
  • 1,5-diMethyl-2-phenyl-1H-pyrazol-3(2H)-one
  • Phenazone 0.25
  • Propyphenazone EP impurity A
  • Antipyrine Vetec(TM) reagent grade, 98%
  • Antipyrine/Phenazone cas:60-80-0
  • 1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
  • 1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
  • ANTIPYRENE
  • ANTIPYRINE
  • ANTIPYRIN(R)
  • AURORA KA-3852
  • 1-Pheny-1-2,3-dimethylpyrazolone-[5],1,2-Di-hydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
  • 1-Phenyl-2,3-dimethyl-5-pyrazolone
  • 1-Phenyl-2,3-dimethylpyrazole-5-one
  • 3-Antipyrine
  • 3-Dimethyl-1-p
  • 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-
  • Anodynin
  • Anodynine
  • Antipirin
  • Antipyrin
  • Antypirine
  • Apirelina
  • Auralgan
  • Azophen
  • Azophene
  • beta-Antipyrine
  • component of Auralgan
  • Dimethyloxychinizin
  • Dimethyloxyquinazine
  • Fenazon
  • Fenazone
  • Methozin
  • Oxydimethylquinazine
  • Parodyne
  • 1-PHENYL-2,3-DIMETHYLPYRAZOL-5-ONE
  • APYRETINE
  • ANTIPYRIN(R), PH EUR
  • ANTIPYRINE CRYSTALLINE
  • ANTIPYRIN(R), CRYSTALLIZED