Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Aminopyrine
AMINOPYRINE · AMINOPHENAZONE · AMIDOPYRINE · 4-DIMETHYLAMINOANTIPYRINE · dimethylaminophenazone · Piramidon · AMINOPYRENE · Aminopyrazolin
식별자 및 물리적 특성
| CAS No. | 58-15-1 |
|---|---|
| 분자식 | C13H17N3O |
| 평균 분자량 | 231.29 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 1 |
|---|---|
| 극성 표면적 | 26.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 17 |
| 형식 전하 | 0 |
| 복잡도 | 343 |
| pH | AQ SOLN IS SLIGHTLY ALKALINE TO LITMUS |
| LogP(분배 계수) | 11.00 |
| LogS | -0.63 |
| 냄새 | ODORLESS |
| Color/Form | LEAFLETS FROM LIGROINCOLORLESS LEAFLETSPRISM OR PLATELETS FROM PETROLEUM ETHER OR ETHYL ACETATE |
| 용해도 | 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/ml |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/. |
| 녹는점 | 225 to 228 °F (NTP, 1992)134.5107-109 °C134.5 °C107-109 °C(lit.) |
| 굴절률 | 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 |
| 끓는 점 | 373.38°C (rough estimate) |
| 밀도 | 1.0744 (rough estimate) |
| 저장 조건 | Refrigerator |
| 물리적 상태 | 결정질 분말, 결정 및/또는 덩어리 |
| pKa(산도 계수) | pKa 5.0 (Uncertain) |
| 색상 | 황백색에서 갈색을 띤다 |
| 용해도 | 5.55g/100mL |
| Merck | 14,474 |
| 안정성 | 안정적인. 강한 산화제, 강산, 강염기와 호환되지 않습니다. 빛에 민감합니다. 수분이나 물이 있는 상태에서 약한 산화제의 작용으로 분해됩니다. |
| 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 |
| NIST | Aminopyrine(58-15-1) |
| EPA | Aminopyrine (58-15-1) |
화학적 성질
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.
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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. |
| 기타 안전 정보 | 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 |
| 운송 라벨(DOT) | Poison |
| 화재 위험 | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| 건강 유해성 | 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.ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992) |
| FDA 요건 | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| 반응성 그룹 | Amides and ImidesAmines, Phosphines, and PyridinesHydrocarbons, Aliphatic Unsaturated |
| Reactivity Profile | 4-DIMETHYLAMINOANTIPYRINE is sensitive to exposure to light. This chemical is readily attacked by mild oxidizing agents in the presence of water. It is incompatible with acacia, apomorphine, aspirin, chloral hydrate, iodine and tannic acid. (NTP, 1992) |
| Air and Water Reactions | Water soluble. |
| Hazard Classes and Categories | Acute Tox. 3 (96.5%)Skin Irrit. 2 (89.5%)Eye Irrit. 2 (89.5%)STOT SE 3 (87.7%) |
| 소화 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 응급 처치 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| 보관 조건 | ...MATERIALS WHICH...CAN DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT...STORED IN COOL, WELL-VENTILATED PLACE, OUT OF...RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD...PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS...ISOLATED FROM EACH OTHER. |
| 비화재 누출 대응 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992) |
| 처리 방법 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Preventive Measures | SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| 체내 부담 | AMINOPYRINE WAS DETECTED IN THE BONE OF A MALE JAPANESE SKELETON AT 12.8 UG/G. |
| 상호 작용 | ELEVATED URINARY LEVELS OF GLUCARIC ACID...OBSERVED IN RAT & GUINEA PIG FOLLOWING...AMINOPYRINE PRETREATMENT... SIMILARLY, PRETREATMENT OF HUMAN SUBJECTS...INCR URINARY...EXCRETIONS....../TETRAHYDROCANNABINOL/ INHIBITED MICROSOMAL OXIDN OF AMINOPYRINE.../FENFLURAMINE/ HAS BEEN SHOWN TO INHIBIT THE METABOLISM OF AMINOPYRINE...AND TO DECREASE THE DISTRIBUTION VOLUME OF ANTIPYRINE IN RATS.PRETREATMENT OF RATS WITH THE AMINOPYRINE DEMETHYLATED METABOLITE 4-(METHYLAMINO)ANTIPYRINE DECREASED THE RATE OF AMINOPYRINE METABOLISM, THAT IS, IT PROLONGED THE ELIMINATION HALF-TIME FOR AMINOPYRINE BINDING SITES ON CYTOCHROME P450.For more Interactions (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | MOST TOXICITY REPORTED FOR THIS DRUG SEEMS TO BE DUE TO HYPERSENSITIVITY, NOTABLY OCCASIONAL FATAL AGRANULOCYTOSIS & ANGIONEUROTIC EDEMA. NO EFFECT ON RED BLOOD CELLS OR HEMOGLOBIN. LARGE DOSES ARE SAID TO CAUSE CONVULSIONS.THERE IS SEVERE INFLAMMATION OF THROAT OFTEN LEADING TO SLOUGHING, FEVER, MALAISE OR PROSTRATION, & MARKED LEUKOPENIA.CASE HISTORY OF FEMALE PATIENT WITH CHEMICALLY INDUCED AGRANULOCYTOSIS.THE FORMATION & POTENTIAL TOXICITY OF THE N-NITROSAMINES ARE DISCUSSED, INCL THE NITROSATION OF DIFFERENT CLASSES OF ORALLY ADMIN DRUGS, SUCH AS AMINOPYRINE, RESULTING IN THE POSSIBLE FORMATION OF CARCINOGENS IN THE BODY.For more Human Toxicity Excerpts (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page. |
| Non-Human Toxicity Excerpts | ...EXPT DESIGNED TO PRODUCE /AGRANULOCYTOSIS/...IN DOGS & OTHER LAB ANIMALS FOLLOWING BOTH ORAL & PARENTERAL USE HAVE BEEN UNSUCCESSFUL. ORAL DAILY DOSAGE IN DOG IS 0.13-0.4 G GIVEN IN DIVIDED DOSES.AMINOPYRINE WAS AMONG COMPOUNDS PRODUCING CHROMOSOME ABERRATIONS AND SISTER CHROMATID EXCHANGES IN CHINESE HAMSTER CELLS....NO DELETERIOUS EFFECTS IN PREGNANT RATS (150 MG/KG), RABBITS (90 MG/KG) & MICE (180 MG/KG) TREATED DAILY DURING MOST OF THEIR GESTATION....FOUND THAT AMINOPYRINE CAUSED EXCITEMENT, INCOORDINATION AND MUSCULAR WEAKNESS IN CATTLE...TOXICITY DUE TO FORMALDEHYDE LIBERATED AS THE DRUG WAS METABOLIZED.For more Non-Human Toxicity Excerpts (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page. |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | CD2625000 |
| 운송 번호(UN) | UN 2811 6.1/PG 3 |
| 독성 | LD50 orally in rats: 1.7 g/kg (Hart) |
| 관세 코드 | 29331190 |
| 위험 문구(R) | 22-36/37/38-21/22 |
| 위험 표시 | Xn |
| 안전 문구(S) | 26-36-36/37/39 |
| 포장분류 | III |
| 위험 등급 | 6.1Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 유해 물질 데이터 | 58-15-1(Hazardous Substances Data) |
용도
용도
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.
일반 설명
Small colorless crystals or white crystalline powder. Aqueous solution slightly alkaline to litmus. pH (5% water solution) 7.5-9. Odorless. Slightly bitter taste.
제조 및 합성 방법
제조 방법
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.