Antipyrine

Antipyrine Basic information
Product Name:Antipyrine
Synonyms: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
CAS:60-80-0
MF:C11H12N2O
MW:188.23
EINECS:200-486-6
Product Categories:Building Blocks;C11;Intermediates & Fine Chemicals;Pharmaceuticals;Lipid signaling;Chemical Synthesis;Aromatics;Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PARODYNE
Mol File:60-80-0.mol
Antipyrine Structure
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
pkapKa 1.4 (Uncertain)
form Crystalline Powder
color White
OdorNone
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.
LogP0.380
CAS DataBase Reference60-80-0(CAS DataBase Reference)
NIST Chemistry ReferenceAntipyrine(60-80-0)
EPA Substance Registry SystemAntipyrine (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
10
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29331190
ToxicityLD50 orally in rats: 1.8 g/kg (Hart)
MSDS Information
ProviderLanguage
Phenazone English
ACROS English
SigmaAldrich English
ALFA English
Antipyrine Usage And Synthesis
Chemical PropertiesColorless crystal or white crystalline powder. Soluble in benzene, ethanol, water, chloroform, slightly soluble in ether. Odorless, slightly bitter.
HistoryAntipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.
UsesAntipyrine 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)
DefinitionChEBI: 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.
PreparationAntipyrine (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.
Synthesis of antipyrine
Brand nameAerol;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 DescriptionAntipyrine 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 ActionsAntipyrine also referred to as phenazone or phenazonum is an anti-inflammatory agent that possesses analgesic, antipyretic and platelet-inhibitory actions.
Safety ProfileA 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 MethodsAntipyrine 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.]
Dacthal 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Aminopyrine 4-ANTIPYRINECARBOXALDEHYDE 4-HYDROXYANTIPYRINE DIANTIPYRYLMETHANE Sildenafil ETHANE Antipyrine, 4-isopropyl-,4-isopropyl-antipyri Phenacetin Dimethyl fumarate Dimethyl sulfoxide Antipyrine Dimethyl ether Dimethyl carbonate Sildenafil citrate Antipyrine, 4-acetamido- Dimethyl sulfate

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