Antipyrine

Bezeichnung:Antipyrine

CAS-Nr60-80-0

Englisch Name:Antipyrine

CBNumberCB8200943

SummenformelC11H12N2O

Molgewicht188.23

MOL-Datei60-80-0.mol

Synonyma

Phenazon

1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on

2,3-Dimethyl-1-phenyl-3-pyrazolin-3-on

Antipyrine physikalisch-chemischer Eigenschaften

Schmelzpunkt	109-111 °C(lit.)
Siedepunkt	319 °C
Dichte	1,19 g/cm³
Brechungsindex	1.5850 (estimate)
storage temp.	2-8°C
Löslichkeit	H2O: soluble1 gm in less than 1ml
Aggregatzustand	Crystalline Powder
pka	pKa 1.4 (Uncertain)
Farbe	White
Wasserlöslichkeit	1000 g/L (20 ºC)
Merck	14,716
BRN	157775
Stabilität	Stable. Incompatible with ammonia, strong acids, alkalies, strong oxidizing agents, metallic salts, phenol.
LogP	0.380
CAS Datenbank	60-80-0(CAS DataBase Reference)
NIST chemische Informationen	Antipyrine(60-80-0)
EPA chemische Informationen	Antipyrine (60-80-0)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36-37/39
RIDADR	3249
WGK Germany	1
RTECS-Nr.	CD2450000
F	10
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29331190
Toxizität	LD50 orally in rats: 1.8 g/kg (Hart)

Gefahreninformationscode (GHS)

Antipyrine Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE KRISTALLE ODER WEISSES PULVER.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger und ätzender Stickstoffoxid-Rauche. Reagiert mit Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Staubes und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden, vor allem als Pulver.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen und die Atemwege. Möglich sind Auswirkungen auf das Blut mit nachfolgender Methämoglobinbildung.
LECKAGE
Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
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.
Verwenden
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.
synthetische
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.
Trademarks
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.
Weltgesundheitsorganisation (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.
Allgemeine Beschreibung
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.
Sicherheitsprofil
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.
läuterung methode
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 Upstream-Materialien And Downstream Produkte

Antipyrine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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