4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on
AMINOPYRINE · AMINOPHENAZONE · AMIDOPYRINE · 4-DIMETHYLAMINOANTIPYRINE · dimethylaminophenazone · Piramidon · AMINOPYRENE · Aminopyrazolin
Identifikatoren & physikalische Daten
| CAS No. | 58-15-1 |
|---|---|
| Summenformel | C13H17N3O |
| Durchschnittliche Molmasse | 231,29 g/mol |
| Monoisotopische Masse | 231,13716217 g/mol |
| SMILES | Cc1c(N(C)C)c(=O)n(-c2ccccc2)n1C |
| InChIKey | RMMXTBMQSGEXHJ-UHFFFAOYSA-N |
| PubChem CID | 6009 |
| ChEMBL | CHEMBL288470 |
| ChEBI | CHEBI:160246 |
| EC No. | 200-365-8 |
| DTXSID | DTXSID7020504 |
| Lokaler Name | 4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-on |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 343 |
| pH | AQ SOLN IS SLIGHTLY ALKALINE TO LITMUS |
| LogP (Verteilungskoeffizient) | 11.00 |
| LogS | -0.63 |
| Geruch | ODORLESS |
| Color/Form | LEAFLETS FROM LIGROINCOLORLESS LEAFLETSPRISM OR PLATELETS FROM PETROLEUM ETHER OR ETHYL ACETATE |
| Löslichkeit | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)54400IN PRESENCE OF WATER, READILY ATTACKED BY MILD OXIDIZING AGENTSADDITION OF SODIUM BENZOATE TO WATER INCR SOLUBILITY1 G SOL IN 1.5 ML ALC, 12 ML BENZENE, 1 ML CHLOROFORM, 13 ML ETHER, 18 ML WATERSOL IN PETROLEUM ETHER2.25e+01 g/LDMF: 5 mg/mlDMSO: 5 mg/mlEthanol: 25 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml5.55 g/100 mL |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/. |
| Schmelzpunkt | 225 to 228 °F (NTP, 1992)134.5107-109 °C134.5 °C107-109 °C(lit.) |
| Brechungsindex | INDEX OF REFRACTION: ALPHA 1.520, GAMMA 1.7321.6140 (estimate) |
| Caco2 Permeability | -4.44 |
| Physical 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. (NTP, 1992)Solid |
| Stability/Shelf Life | STABLE IN AIR, BUT AFFECTED BY LIGHT |
| Siedepunkt | 373.38°C (rough estimate) |
| Dichte | 1.0744 (rough estimate) |
| Lagerbedingungen | Refrigerator |
| Aggregatzustand | Crystalline Powder, Crystals and/or Chunks |
| pKa (Säurekonstante) | pKa 5.0 (Uncertain) |
| Farbe | Off-white to brownish |
| 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. |
| InChI | 1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3 |
| InChIKey | RMMXTBMQSGEXHJ-UHFFFAOYSA-N |
| SMILES | CN(C)C1=C(C)N(C)N(c2ccccc2)C1=O |
| CAS Datenbank | 58-15-1(CAS DataBase Reference) |
| NIST chemische Informationen | Aminopyrine(58-15-1) |
| EPA chemische Informationen | Aminopyrine (58-15-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (96.5%): Toxic if swallowed [Danger Acute toxicity, oral]H315 (89.5%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (89.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (87.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 57 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | IMAP assessments - 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessmentIMAP assessments - 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: Human health tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include allergic reactions, strong spasmolytic effect on smooth muscle of peripheral blood vessels, irritability, palsy, copious sweating, dilated pupils, sharp drop then rise in body temperature, dysuria, dyspnea, anxiety, tenesmus, urinary frequency, intermittent fever, fatty infiltration of the liver, heart muscle degeneration and death due to circulatory failure following cardiovascular collapse. Agranulocytosis often occurs. Ingestion may cause central nervous system stimulation, vomiting, convulsions, cyanosis, tinnitus, leukopenia, kidney damage and coma. Ingestion may also lead to nausea, mental disturbances, methemoglobinemia, chocolate-colored blood, dizziness, epigastric pain, difficulty in hearing, thready pulse and liver damage. Other symptoms reported via ingestion include hemolytic anemia, porphyria and severe gastrointestinal bleeding. Bone marrow depression also occurs. Rare eye effects include acute transient myopia. Chronic symptoms include anorexia, edema, oliguria, urticaria, hypersensitivity, aplastic anemia, sore throat, fever, pharyngeal membrane, jaundice enlargement of the liver and spleen, exfoliative dermatitis, gastric or duodenal erosion with perforation or bleeding, adrenal necrosis, thrombocytopenic purpura and acute leukemia. |
Anwendungen & Verwendung
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.
Herstellung & Synthese
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.