Antipyrine Chemical Properties

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

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)

Safety Information

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)

MSDS

• Language:English Provider:Phenazone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Antipyrine Usage And Synthesis

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(60-80-0)Related Product Information

• 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