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Substance Name: Aminopyrine [JAN:NF]
RN: 58-15-1
UNII: 01704YP3MO
InChIKey: RMMXTBMQSGEXHJ-UHFFFAOYSA-N

Note

  • A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.

Molecular Formula

  • C13-H17-N3-O

Molecular Weight

  • 231.2973
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Results Name

  • Aminopyrine [JAN:NF]

Name of Substance

  • Aminophenazone [INN]
  • Aminopyrine
  • Aminopyrine [JAN:NF]

MeSH Heading

  • Aminopyrine

Synonyms

  • 1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone
  • 1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one
  • 2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone
  • 3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole
  • 3-Pyrazolin-5-one, 4-(dimethylamino)-2,3-dimethyl-1-phenyl-
  • 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
  • 4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
  • 4-(Dimethylamino)antipyrine
  • 4-Dimethylamino-1-phenyl-2,3-dimethylpyrazolone
  • 4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
  • 4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone
  • 4-Dimethylaminophenazone
  • Amidazofen
  • Amidazophen
  • Amidazophene
  • Amidazophenum
  • Amidofebrin
  • Amidofen
  • Amidophen
  • Amidophenazone
  • Amidopyrazoline
  • Amidopyrin
  • Amidopyrine
  • Amidopyrinum
  • Aminofenazona
  • Aminofenazona [INN-Spanish]
  • Aminofenazone
  • Aminofenazone [Italian]
  • Aminophenazon
  • Aminophenazon [German]
  • Aminophenazone
  • Aminophenazonum
  • Aminophenazonum [INN-Latin]
  • Aminopyrene
  • Aminopyrin
  • Aminopyrine
  • Aminopyrinum
  • Anafebrina
  • Antipyrine, 4-(dimethylamino)-
  • Brufaneuxol
  • CCRIS 2907
  • Dereuma
  • Dimapyrin
  • Dimethylamino-analgesine
  • Dimethylaminoantipyrine
  • Dimethylaminoazophene
  • Dimethylaminophenazon
  • Dimethylaminophenazon [German]
  • Dimethylaminophenazone
  • Dimethylaminophenyldimethylpyrazolin
  • Dimethylaminophenyldimethylpyrazolone
  • Dipirin
  • Dipyrin
  • Dipyrine
  • EINECS 200-365-8
  • Eufibron
  • Febrinina
  • Febron
  • HSDB 2135
  • Hyparon
  • Itamidone
  • Mamallet-A
  • Netsusarin
  • Novamidon
  • NSC 4993
  • Piramidon
  • Pirazon
  • Piridol
  • Piromidina
  • Polinalin
  • Pyradone
  • Pyramidon
  • Pyramidone
  • UNII-01704YP3MO

Systematic Names

  • 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
  • 4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
  • Aminophenazone
  • Aminopyrine
  • Antipyrine, 4-(dimethylamino)-

Registry Numbers

CAS Registry Number

  • 58-15-1

FDA UNII

  • 01704YP3MO

Other Registry Number

  • 144574-10-7

System Generated Number

  • 0000058151

Structure Descriptors

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

Cc1c(c(=O)n(n1C)c2ccccc2)N(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Journal of Pharmacology and Experimental Therapeutics. Vol. 39, Pg. 177, 1930.
cat LDLo oral 100mg/kg (100mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 73, Pg. 312, 1941.
dog LD50 intravenous 121mg/kg (121mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
dog LD50 oral 220mg/kg (220mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
frog LDLo parenteral 900mg/kg (900mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
guinea pig LD50 intravenous 130mg/kg (130mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 88, Pg. 142, 1951.
guinea pig LD50 oral 910mg/kg (910mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 84, Pg. 351, 1954.
guinea pig LDLo subcutaneous 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
hamster LD50 intraperitoneal 380mg/kg (380mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1024, 1970.
mammal (species unspecified) LD50 intraperitoneal 300mg/kg (300mg/kg)   Farmatsevtichnii Zhurnal Vol. 29(2), Pg. 25, 1974.
man LDLo unreported 220mg/kg (220mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LC50 inhalation 20410mg/m3 (20410mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(10), Pg. 36, 1969.
mouse LD50 intramuscular 306mg/kg (306mg/kg) BEHAVIORAL: ANALGESIA Oyo Yakuri. Pharmacometrics. Vol. 13, Pg. 109, 1977.
mouse LD50 intraperitoneal 169mg/kg (169mg/kg)   Russian Pharmacology and Toxicology Vol. 35, Pg. 293, 1972.
mouse LD50 intravenous 78mg/kg (78mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 1011, 1978.
mouse LD50 oral 300mg/kg (300mg/kg)   Pharmaceutical Chemistry Journal Vol. 30, Pg. 374, 1996.
mouse LD50 subcutaneous 248mg/kg (248mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 494, 1977.
mouse LD50 unreported 300mg/kg (300mg/kg)   Farmakologiya i Toksikologiya Vol. 39, Pg. 148, 1976.
rabbit LD50 intravenous 80mg/kg (80mg/kg)   Bollettino Chimico Farmaceutico. Vol. 102, Pg. 602, 1963.
rabbit LD50 oral 600mg/kg (600mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 1011, 1978.
rabbit LDLo subcutaneous 250mg/kg (250mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 intramuscular 340mg/kg (340mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.
rat LD50 intraperitoneal 190mg/kg (190mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 442, 1972.
rat LD50 intravenous 98mg/kg (98mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 1011, 1978.
rat LD50 oral 285mg/kg (285mg/kg)   Russian Pharmacology and Toxicology Vol. 51, Pg. 183, 1988.
rat LD50 rectal 310mg/kg (310mg/kg)   Pharmazie. Vol. 18, Pg. 807, 1963.
rat LD50 subcutaneous 295mg/kg (295mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 229, 1958.
rat LD50 unreported 176mg/kg (176mg/kg)   Farmakologiya i Toksikologiya Vol. 39, Pg. 14, 1976.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 134.5 deg C   EXP
pKa Dissociation Constant 5 (none)   EXP
log P (octanol-water) 1 (none)   EXP
Water Solubility 5.44E+04 mg/L 30 EXP
Vapor Pressure 2.77E-06 mm Hg 25 EST
Henry's Law Constant 1.38E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.62E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.