| Identification | More | [Name]
Aminophenazone | [CAS]
58-15-1 | [Synonyms]
4-(DIMETHYLAMINO)-1,5-DIMETHYL-2-PHENYL-3-PYRAZOLONE
4-DIMETHYLAMINO-2,3-DIMETHYL-1-PHENYL-3-PYRAZOLIN-5-ONE
4-(DIMETHYLAMINO)-2,3-DIMETHYL-1-PHENYL-5-PYRAZOLONE
4-DIMETHYLAMINO-2,3-DIMETHYL-1-PHENYLPYRAZOL-5-ONE
4-DIMETHYLAMINOANTIPYRINE
4-(DIMETHYLAMINO)PHENAZONE
AMIDOPYRINE
AMINOPHENAZONE
AMINOPYRINE
PYRAMIDON
(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
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- | [EINECS(EC#)]
200-365-8 | [Molecular Formula]
C11H13N3O | [MDL Number]
MFCD00003142 | [Molecular Weight]
203.24 | [MOL File]
58-15-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
107-109 °C(lit.)
| [Boiling point ]
373.38°C (rough estimate) | [density ]
1.0744 (rough estimate) | [refractive index ]
1.6140 (estimate) | [storage temp. ]
Refrigerator | [solubility ]
DMF: 5 mg/ml; DMSO: 5 mg/ml; Ethanol: 25 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | [form ]
Crystalline Powder, Crystals and/or Chunks | [pka]
pKa 5.0 (Uncertain) | [color ]
Off-white to brownish | [Stability:]
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. | [Water Solubility ]
5.55 g/100 mL | [Sensitive ]
Air & Light Sensitive | [Merck ]
14,474 | [InChIKey]
RMMXTBMQSGEXHJ-UHFFFAOYSA-N | [CAS DataBase Reference]
58-15-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Aminopyrine(58-15-1) | [EPA Substance Registry System]
58-15-1(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 .
R21/22:Harmful in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
CD2625000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29331190 | [Safety Profile]
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. | [Hazardous Substances Data]
58-15-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 1.7 g/kg (Hart) |
| Hazard Information | Back Directory | [General Description]
Small colorless crystals or white crystalline powder. Aqueous solution slightly alkaline to litmus. pH (5% water solution) 7.5-9. Odorless. Slightly bitter taste. | [Reactivity Profile]
4-DIMETHYLAMINOANTIPYRINE(58-15-1) is sensitive to exposure to light. This chemical is readily attacked by mild oxidizing agents in the presence of water. 4-DIMETHYLAMINOANTIPYRINE(58-15-1) is incompatible with acacia, apomorphine, aspirin, chloral hydrate, iodine and tannic acid. | [Air & Water Reactions]
Water soluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, 4-DIMETHYLAMINOANTIPYRINE is probably combustible. | [Chemical Properties]
white crystalline powder | [Application]
Oxidation by Fe(VI) has potential to remove N-nitrosodiumethylamine precursors, including 4-dimethylaminoantipyrine, from drinking water. 4-Dimethylaminoantipyrine is itself an effective scavenger of reactive nitrogen compounds nitric oxide and peroxynitrite, important in the inflammatory response. | [Uses]
Antipyretic; analgesic. | [Uses]
Antipyretic;ACTH secretor | [Definition]
ChEBI: 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 proper
ies. | [Preparation]
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. | [Brand name]
Adexogan;Agevis;Algimicin anttitermico;Amidazopen;Amidozen;Anoixal;Antigripina;Areumal;Axiston;Balbion;Barsedan;Baukal suppositories;Bayer 1387 p;Bronchisan;Brufaneuseol;Butapyrine;Capsyka dr knapf;Capysal;Chinopyrin;Cibalgin;Ciclazon;Clinit;Coffan;Compral;Cusayth;Demolpas;Dentigoa;Depiral c;Dexa escopyrin;Dha 51;Dialpyrin;Digisab;Dimametten;Dimopyrin;Diprin;Dolo-attirin;Dolo-optineural;Dolorphen;Dolovosano;Donobin;Duerin;Dysmensan;Escopyrinus;Espasnatex;Eufibran;Euprogan;Febren;Febrosolvin;Fenodone;Fever;Flivalgin;Flumil;Framidone;Ftalazon;Funapon;Galenopyrin;Glucopirina;Glucopitina;Helvagit-f;Hemicraneal;Hisense-p;Influnal depot;Inst;Irgapyrine;Isoftal;Kalmine;Katareuma;Lagaflex;Latepyrine;Lauroanginol;Manslu;Medispanmin;Meloka;Neuro-demoplast;Nifedon;Nikartrone;Nostress;Optineural(analgesic);Optipax;Osadrine;Osmotipax;P.s.b.p.;Piracodid;Piradenil;Piradol;Pirasco;Piraseptolo. | [World Health Organization (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) | [Biochem/physiol Actions]
Antipyrine was found to be nonmutagenic when screened against Salmonella typhimurium tester strains TA100, TA98, TA97, TA102 and TA104. | [Metabolism]
Aminopyrine is very slowly metabolized by normal neonate. In older infants, a higher amount of exhaled 13-CO2 is observed. In chicken aminopyrine-N-demethylase inhibits the activities of some important P-450 enzymes. It is mostly metabolized through N-demethylation to form monomethyl-4-antipyrine and formaldehyde, which can be measured by colorimetry Nash. Aminopyrine Ndemethylase is almost equal to isoform CYP-3A4 and closely linked to the methylation reaction of drugs.
why Aminopyrine Banned? | [Purification Methods]
It crystallises from pet ether, sublimes between 80o and 90o, and forms metal complexes. [Beilstein 25 H 452, 25 III/IV 3555.] |
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