58-15-1

Name	Aminophenazone
CAS	58-15-1
EINECS(EC#)	200-365-8
Molecular Formula	C11H13N3O
MDL Number	MFCD00003142
Molecular Weight	203.24
MOL File	58-15-1.mol

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-

Chemical Properties

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
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

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 . less more
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 . less more
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. less more
Hazardous Substances Data	58-15-1(Hazardous Substances Data)
Toxicity	LD50 orally in rats: 1.7 g/kg (Hart) less more

Raw materials And Preparation Products

Hazard Information

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.]

Material Safety Data Sheet(MSDS)

Spectrum Detail

Well-known Reagent Company Product Information

Send Inquriy