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Aminopyrine

HCID 178785919
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
91419-95-3
標準SMILES
Cc1c(N(C)C)c(=O)n(-c2ccccc2)n1C
InChIKey
RMMXTBMQSGEXHJ-UHFFFAOYSA-N
分子式
C13H17N3O
平均分子量
231.29 g/mol

概要

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)

名称と識別子

優先名称
Aminopyrine
IUPAC
4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one
英語名
4-DiMethylaMino Antipyrine-d6
分子式
C13H17N3O
分子量
231.29358

名称と別名

aminophenazoneAMINOPYRINEAmidopyrine58-15-14-DimethylaminoantipyrineDipyrineAmidazopheneAmidopyrazolineAminopyrinPyramidonDimethylaminoantipyrineAmidazophen
名称をさらに表示
Anafebrina-d6AMinopyrine-d6Brivudine Impurity 43(DiMethylaMino-d6)phenazone(DiMethylaMino-d6)analgesine4-DiMethylaMino Antipyrine-d6[2H6]-4-Dimethylamino Antipyrine4-Dimethylaminoantipyrine-D6(Aminophenazone-D6)4-(DiMethylaMino-d6)-2,3-diMethyl-1-phenyl-3-pyrazolin-5-one4-(DiMethylaMino-d6)-1,2-dihydro-1,5-diMethyl-2-phenyl-3H-pyrazol-3-one
AmidophenBrufaneuxolItamidoneDereumaFebronDimethylaminoazopheneAmidofebrinAmidophenazone

データベース識別子

CAS
91419-95-3
ChEMBL
CHEMBL288470
ChEBI
CHEBI:160246
UNII
01704YP3MO
EC Number

物性

構造計算による物性

XLogP
1
極性表面積
26.8 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
2
重原子数
17
形式電荷
0
複雑度
343

実験および物理化学的性質

Drugs · 3 件

DEA NFLIS-Drug Category -> Analgesics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Metamizole

pHAQ SOLN IS SLIGHTLY ALKALINE TO LITMUS
SpringerMaterials PropertiesCrystal structure
LogP · 2 件

1.00

0.89

OdorODORLESS
Color/Form · 3 件

LEAFLETS FROM LIGROIN

COLORLESS LEAFLETS

PRISM OR PLATELETS FROM PETROLEUM ETHER OR ETHYL ACETATE

Solubility · 5 件

greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)

IN PRESENCE OF WATER, READILY ATTACKED BY MILD OXIDIZING AGENTS; ADDITION OF SODIUM BENZOATE TO WATER INCR SOLUBILITY

1 G SOL IN 1.5 ML ALC, 12 ML BENZENE, 1 ML CHLOROFORM, 13 ML ETHER, 18 ML WATER

SOL IN PETROLEUM ETHER

2.25e+01 g/L

Human DrugsPharmaceuticals
DecompositionWHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/.

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (96.5%): Toxic if swallowed [Danger Acute toxicity, oral]

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.

危険有害性情報

Regulatory Information · 2 件

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.

Other Safety InformationIMAP assessments - 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 件

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.

化学と産業

薬理情報

ATC Code · 3 件

N02BB03

N - Nervous system

QN - Nervous system

PharmacodynamicsAminophenazone exhibits analgesic, anti-inflammatory, and antipyretic properties.
Mechanism of Action · 2 件

Aminophenazone is metabolized very slowly by normal newborn babies. In older infants, a higher amount of exhaled 13-CO2 is observed.

VET: AMIDOPYRINE IS KNOWN TO CAUSE AGRANULOCYTOSIS IN MAN, BUT IT HAS BEEN FOUND IMPOSSIBLE TO REPRODUCE THIS EFFECT IN THE DOG & OTHER LABORATORY ANIMALS.

Metabolism/Metabolites · 4 件

...URINARY METABOLITE OF AMINOPYRINE HAS BEEN IDENTIFIED AS 4-ACETYLAMINO-3-METHYL-1-PHENYLPYRAZOLONE IN TREATED SUCKLINGS, INFANTS, & ADULT. ... FORMATION.../OF THIS METABOLITE/ IMPLICATES EXHAUSTIVE OXIDATIVE N-DEALKYLATION OF.../AMINOPYRINE/ FOLLOWED BY ACETYLATION OF RELEASED AMINO-GROUP.

...BIOTRANSFORMATION OF AMINOPYRINE. MAN & DOG EXCRETE RUBAZONIC ACID...& N-METHYLRUBAZONIC ACID...WHOSE FORMATION INVOLVES NUMBER OF METABOLIC STEPS. FOLLOWING FORMATION OF 4-HYDROXYANTIPYRINE, THIS METABOLITE IS N-DEMETHYLATED... & DEHYDROGENATED TO HYPOTHETICAL DIKETO INTERMEDIATE...LATTER CMPD...UNDERGOES FINAL COUPLING...WITH ANOTHER METABOLITE, 4-AMINOANTIPYRINE...

CIRCADIAN RHYTHMS...OFTEN SEEN WITHIN A GIVEN ANIMAL SPECIES. VARIATION IN RATE OF METABOLISM IS OFTEN CORRELATED WITH VARIATIONS IN ENDOCRINE FUNCTION AS INFLUENCED BY THE LIGHT-DARK CYCLE TO WHICH THE ANIMAL IS EXPOSED. ...IN VITRO METABOLISM OF...AMINOPYRINE...BY THE HEPATIC CYTOCHROME P450 MONOOXYGENASE SYSTEM OF RATS IS VARIABLE DEPENDING ON THE TIME OF DAY OF SACRIFICE OF THE ANIMAL.

AMINOPHENAZONE AND ITS METABOLITES; 4-AMINOANTIPYRINE, N-ACETYLAMINOANTIPYRINE AND 4-FORMYLAMINOANTIPYRINE WERE DETECTED IN STUDIES ON HEALTHY SUBJECTS.

Absorption, Distribution and Excretion · 4 件

IT IS ABSORBED RAPIDLY FOLLOWING ORAL ADMIN...EXCRETED IN URINE UNCHANGED OR CONJUGATED WITH GLUCURONIC & SULFURIC ACIDS.

...SLIGHTLY BOUND TO PLASMA PROTEIN...

THREE METABOLITES OF AMINOPYRINE WERE DETECTED IN THE URINE, SERUM, AND SALIVA OF HEALTH SUBJECTS AFTER INGESTION OF AMINOPYRINE.

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
200-365-8
Nikkaji
J2.331K
Melting Point · 3 件

225 to 228 °F (NTP, 1992)

107-109 °C

134.5 °C

Refractive IndexINDEX OF REFRACTION: ALPHA 1.520, GAMMA 1.732
Physical Description · 2 件

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

物理化学的性質

溶解性
DMSO (Slightly), Methanol (Slightly)
外見
Solid
色
White to Light Yellow
FDA Requirements · 1 件

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 amended; 21 U.S.C. 321-392).

Reactive GroupAmides and Imides
Reactivity Profile · 1 件

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 ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 3 (96.5%)

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

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.

Storage Conditions · 1 件

...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.

Nonfire Spill Response · 1 件

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.

Disposal Methods · 1 件

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 · 1 件

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 EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 件

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)

毒性情報

Body BurdenAMINOPYRINE WAS DETECTED IN THE BONE OF A MALE JAPANESE SKELETON AT 12.8 UG/G.
Interactions · 5 件

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 · 5 件

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 · 5 件

...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.

法規制情報

FDA Requirements · 1 件

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 amended; 21 U.S.C. 321-392).

IMMEDIATELY AFTER INJECTION OF AMINOPYRINE-(14)C INTO RATS A UNIFORM DISTRIBUTION OF RADIOACTIVITY IN THE BODY WAS RECORDED. AFTER 30 MINUTES, A PREFERENTIAL LOCALIZATION OF RADIOACTIVITY WAS FOUND IN THE NASAL MUCOSA AND LIVER.

Cellular LocationsMembrane

用途と製造

Uses · 2 件

MEDICATION (VET)

MEDICATION

U.S. Imports · 2 件

(1972) 1.5X10+6 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 6.51X10+5 GRAMS (PRINCPL CUSTMS DISTS)

Consumption PatternsESSENTIALLY 100% AS A MEDICINAL (1976)
Methods of ManufacturingPREPD FROM ANTIPYRINE BY TREATING WITH SODIUM NITRITE IN ACID SOLN, REDUCING NITROSO COMPD TO AMINE WITH ZINC & ACETIC ACID, PURIFYING AMINE AS BENZYLIDENE DERIV, HYDROLYZING BENZYLIDENE COMPD WITH HCL & METHYLATING AMINO GROUP
Use Classification · 2 件

Pharmaceuticals

Pharmaceuticals -> Nervous System -> Analgesics -> Pyrazolones

General Manufacturing Information · 6 件

3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: ACTIVE

"OVER-THE-COUNTER" SALE OF AMINOPYRINE IN US...PROHIBITED SINCE 1938, & FED REGULATIONS REQUIRE THAT PREPN...BEAR WARNING ON LABELS STATING THAT DRUG MAY CAUSE FATAL AGRANULOCYTOSIS.

INCOMPATIBILITIES: IS INCOMPATIBLE WITH MANY ALKALOIDAL PRECIPITANTS, OXIDIZING AGENTS & MERCURY SALTS...

CRYSTAL AMIDOPHEN UV IRRADIATED FOR 300 HR CHANGED TO AN ORANGE-BROWN PRODUCT FROM WHICH 3 YELLOW DEGRADATION PRODUCTS WERE ISOLATED.

THE PERMEATION OF AMINOPYRINE THROUGH AN ARTIFICIAL INTESTINAL MEMBRANE WAS HIGHER THAN THAT THROUGH AN ARTIFICIAL GASTRIC MEMBRANE.

THE TRANSFER RATE OF BARBITAL FROM AQUEOUS TO BENZENE PHASE WAS ACCELERATED BY THE ADDITION OF AMINOPYRINE.

応用分野

使用Labelled 4-Dimethylaminoantipyrine(D460890). Antipyretic; analgesic.