| Identification | More | [Name]
Antipyrine | [CAS]
60-80-0 | [Synonyms]
1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
1,5-DIMETHYL-2-PHENYL-3-PYRAZOLONE
1-PHENYL-2,3-DIMETHYLPYRAZOL-5-ONE
2,3-DIMETHYL-1-PHENYL-3-PYRAZOLIN-5-ONE
2,3-DIMETHYL-1-PHENYL-5-PYRAZOLONE
ANALGESINE
ANTIPYRENE
ANTIPYRINE
ANTIPYRIN(R)
AURORA KA-3852
OXYDIMETHYLQUINIZINE
PHENAZONE
PHENAZONUM
1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-on
1,5-Dimethyl1-2-phenyl-3-pyrazolone
1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
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 | [EINECS(EC#)]
200-486-6 | [Molecular Formula]
C11H12N2O | [MDL Number]
MFCD00003146 | [Molecular Weight]
188.23 | [MOL File]
60-80-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [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 | [Odor]
None | [Stability:]
Stable. Incompatible with ammonia, strong acids, alkalies, strong oxidizing agents, metallic salts, phenol. | [biological source]
rabbit | [Water Solubility ]
1000 g/L (20 ºC) | [Usage]
Analgesic | [Merck ]
14,716 | [BRN ]
157775 | [LogP]
0.380 | [CAS DataBase Reference]
60-80-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Antipyrine(60-80-0) | [EPA Substance Registry System]
60-80-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
3249 | [WGK Germany ]
1
| [RTECS ]
CD2450000
| [F ]
10 | [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29331190 | [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. | [Toxicity]
LD50 orally in rats: 1.8 g/kg (Hart) |
| Hazard Information | Back Directory | [Chemical Properties]
White Powder | [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. | [Uses]
Analgesic; used to test hepatic drug-metabolizing activity. | [Definition]
ChEBI: A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at C-1 and C-5 and with a phenyl group at N-2. | [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]
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. | [Biochem/physiol Actions]
Antipyrine also referred to as phenazone or phenazonum is an anti-inflammatory agent that possesses analgesic, antipyretic and platelet-inhibitory actions. | [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.] |
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