4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on

Aminopyrine Struktur
58-15-1
CAS-Nr.
58-15-1
Bezeichnung:
4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on
Englisch Name:
Aminopyrine
Synonyma:
AMINOPYRINE;AMINOPHENAZONE;AMIDOPYRINE;4-DIMETHYLAMINOANTIPYRINE;dimethylaminophenazone;Piramidon;Aminopyrazolin;Dimethylaminoantipyrine;4-DiMethylaMino-1,5-diMethyl-2-phenyl-1-pyrazolone;2-dihydro-4-(N.,N-dimethylamino-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
CBNumber:
CB1476086
Summenformel:
C13H17N3O
Molgewicht:
231.29
MOL-Datei:
58-15-1.mol

4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on Eigenschaften

Schmelzpunkt:
107-109 °C(lit.)
Siedepunkt:
373.38°C (rough estimate)
Dichte
1.0744 (rough estimate)
Brechungsindex
1.6140 (estimate)
storage temp. 
Refrigerator
Löslichkeit
DMF: 5 mg/ml; DMSO: 5 mg/ml; Ethanol: 25 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
Aggregatzustand
Crystalline Powder, Crystals and/or Chunks
pka
pKa 5.0 (Uncertain)
Farbe
Off-white to brownish
Wasserlöslichkeit
5.55 g/100 mL
Sensitive 
Air & Light Sensitive
Merck 
14,474
Stabilität:
Stable. Incompatible with strong oxidizing agents, strong acids, strong bases. Light sensitive. Degrades under the action of mild oxidizing agents in the presence of moisture or water.
InChIKey
RMMXTBMQSGEXHJ-UHFFFAOYSA-N
CAS Datenbank
58-15-1(CAS DataBase Reference)
NIST chemische Informationen
Aminopyrine(58-15-1)
EPA chemische Informationen
Aminopyrine (58-15-1)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn
R-Sätze: 22-36/37/38-21/22
S-Sätze: 26-36-36/37/39
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS-Nr. CD2625000
TSCA  Yes
HazardClass  6.1
PackingGroup  III
HS Code  29331190
Giftige Stoffe Daten 58-15-1(Hazardous Substances Data)
Toxizität LD50 orally in rats: 1.7 g/kg (Hart)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.

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.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

Chemische Eigenschaften

White leaf-like crystals or crystalline powder. Odorless, slightly bitter taste. It is stable in the air, but will deteriorate in sunlight. When there is moisture, it is easy to chemically react with weak oxidants. Soluble in alcohol, chloroform, benzene and ether, soluble in water. The solubility in water increases with the addition of sodium benzoate. Aqueous solutions are weakly alkaline to litmus. The melting point is 107-109°C.

Verwenden

Aminopyrine is used as an antipyretic and analgesic drug. It belongs to the pyrazolone derivatives having a most toxic and most dangerous analgesic effect and it is a non-narcotic drug. Due to strong adverse effects, its single medicine preparation is gradually replaced by compound preparation.

synthetische

Aminopyrine is synthesized from 4-Aminoantipyrine by catalytic hydrogenation (alkylation). Water is firstly added to the dissolving tank, heated to 50-60°C, put into 4-Aminoantipyrine under stirring, and poured into the hydrogenation tank after complete dissolving. Wash the dissolving tank with water, mix it with the nickel catalyst, and then add it to the hydrogenation tank. The hydrogenation tank was evacuated, then the vacuum valve was closed, hydrogen was introduced, and stirring was started. When the pressure rose to 0.245MPa, the hydrogen was stopped. Add formaldehyde and continue to feed hydrogen. The speed of adding formaldehyde is based on the standard of 1.8-2 cubic meters of hydrogen absorption per 5L of formaldehyde, and the reaction temperature is controlled at 60-85°C. After passing the test, filter by pressure, cool the filtrate to below 25°C, and separate out crystals, which are then filtered to obtain the crude aminopyrine. The crude aminopyrine, ethanol, and activated carbon were heated to 75-80°C, stirred for 1 hour, and filtered under pressure. The filtrate was cooled to 10°C, crystals were precipitated, filtered, washed with ethanol, and air-dried to obtain aminopyrine.

Definition

ChEBI: Aminopyrine is a pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an environmental contaminant and a xenobiotic. It is a tertiary amino compound and a pyrazolone.

Weltgesundheitsorganisation (WHO)

Aminophenazone, a pyrazolone derivative, has been used as an antiinflammatory and analgesic agent for over a century. Its use has been associated with cases of bone marrow depression and agranulocytosis and more recently it has been claimed to have a carcinogenic potential. Products containing aminophenazone have been formally withdrawn in many countries and marketing has been voluntarily suspended in others. Elsewhere, however, proprietary preparations containing this ingredient may remain available. (Reference: (WHODI) WHO Drug Information, 3, 9, 1977)

Allgemeine Beschreibung

Small colorless crystals or white crystalline powder. Aqueous solution slightly alkaline to litmus. pH (5% water solution) 7.5-9. Odorless. Slightly bitter taste.

Air & Water Reaktionen

Water soluble.

Reaktivität anzeigen

Aminophenazone is sensitive to exposure to light. Aminophenazone is readily attacked by mild oxidizing agents in the presence of water. Aminophenazone is incompatible with acacia, apomorphine, aspirin, chloral hydrate, iodine and tannic acid.

Brandgefahr

Flash point data for Aminophenazone are not available; however, Aminophenazone is probably combustible.

Sicherheitsprofil

Human poison by unspecified route. Experimental poison by ingestion, subcutaneous, intramuscular,intravenous, and intraperitoneal routes. Moderately toxic by parenteral route. Experimental teratogenic and reproductive effects. Questionable carcinogen when mixed with NaNO2 (1:l). Mutation data reported. Can cause bone marrow depression resulting in leucopenia. Has been implicated in development of aplastic anemia. A tranquilizer. When heated to decomposition it emits toxic fumes of NOx.

läuterung methode

It crystallises from pet ether, sublimes between 80o and 90o, and forms metal complexes. [Beilstein 25 H 452, 25 III/IV 3555.]

4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte

58-15-1(4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on)Verwandte Suche:


  • (Dimethylamino)phenazone
  • 1,5-Dimethyl-2-phenyl-4-dimethylamino-3-pyrazolone
  • 1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone
  • 1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone
  • 1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one
  • 4-DIMETHYLAMINO-2,3-DIMETHYL-1-PHENYLPYRAZOL-5-ONE BP2000
  • 1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazolone-5
  • 2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone
  • 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
  • 3-keto-1,5-Dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole
  • 3-Pyrazolin-5-one, 4-(dimethylamino)-2,3-dimethyl-1-phenyl-
  • 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-on
  • 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
  • 4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
  • 4-(dimethylamino)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-on
  • 4-(dimethylamino)-antipyrin
  • 4-Dimethylamino-1-phenyl-2,3-dimethylpyrazolone
  • 4-Dimethylaminoantipyrine;Aminopyrine
  • Aminopyrinum
  • Amidopyrinum
  • 4-DIMETHYLAMINOANTIPYRINE FREE BASE
  • Amidazofen
  • Amidazophen
  • Amidazophene
  • Amidofebrin
  • Amidofen
  • Amidophen
  • Amidophenazone
  • Amidopyrazoline
  • Amidopyrin
  • Aminofenazone
  • Aminophenazon
  • Aminopyrin
  • Anafebrina
  • Antipyrine, 4-(dimethylamino)-
  • Brufaneuxol
  • Dereuma
  • Dimapyrin
  • Dimethylamino-analgesine
  • Dimethylaminoazophene
  • Dimethylaminophenazon
  • Dimethylaminophenyldimethylpyrazolin
  • Dimethylaminophenyldimethylpyrazolone
  • Dimethylaminophenyldimethylpyrazone
  • Dipirin
  • Dipyrin
  • Dipyrine
  • Eufibron
  • Febrinina
  • Febron
  • Hyparon
  • Itamidone
  • Mamallet-A
  • Netsusarin
  • Novamidon
  • Pirazon
  • Piridol
  • Piromidina
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