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Aminopyrine

PubChem CID
6009
Structure
Aminopyrine_small.png
Aminopyrine_3D_Structure.png
Molecular Formula
Synonyms
  • AMINOPYRINE
  • aminophenazone
  • Amidopyrine
  • 58-15-1
  • 4-Dimethylaminoantipyrine
Molecular Weight
231.29 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
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)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Aminophenazone is 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 properties. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an environmental contaminant and a xenobiotic. It is a tertiary amino compound and a pyrazolone.
Aminophenazone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties that carries a risk of agranulocytosis. In biomedical applications, radiolabelled (13C-labeled) aminophenazone has been used in breath tests to measure the cytochrome P-450 metabolic activity in liver function tests. The FDA suspended the use of aminophenazone due to its association with agranulocytosis, a life-threatening side effect.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Aminopyrine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RMMXTBMQSGEXHJ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C13H17N3O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

58-15-1
83-07-8

2.3.2 Deprecated CAS

144574-10-7

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 UN Number

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DrugBank ID

2.3.9 DSSTox Substance ID

2.3.10 HMDB ID

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 NSC Number

2.3.16 PharmGKB ID

2.3.17 Pharos Ligand ID

2.3.18 Wikidata

2.3.19 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Amidazophen
  • Amidophen
  • Amidophenazon
  • Amidopyrine
  • Aminofenazone
  • Aminophenazone
  • Aminopyrine
  • Dimethyl N aminoantipyrine
  • Dimethyl-N-aminoantipyrine
  • Dimethylaminoantipyrine
  • Dimethylaminophenazone
  • Dipyrine
  • Eufibron

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
231.29 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
231.137162174 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
231.137162174 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
17
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
343
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 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)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Solid

3.2.2 Color / Form

LEAFLETS FROM LIGROIN
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 77
COLORLESS LEAFLETS
Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand Reinhold, 1975., p. 384
PRISM OR PLATELETS FROM PETROLEUM ETHER OR ETHYL ACETATE
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-126

3.2.3 Odor

ODORLESS
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1053

3.2.4 Melting Point

225 to 228 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
134.5 °C
PhysProp
107-109 °C
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 77
134.5 °C

3.2.5 Solubility

greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
54400 mg/L (at 30 °C)
YALKOWSKY,SH & DANNENFELSER,RM (1992)
IN PRESENCE OF WATER, READILY ATTACKED BY MILD OXIDIZING AGENTS; ADDITION OF SODIUM BENZOATE TO WATER INCR SOLUBILITY
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 77
1 G SOL IN 1.5 ML ALC, 12 ML BENZENE, 1 ML CHLOROFORM, 13 ML ETHER, 18 ML WATER
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 77
SOL IN PETROLEUM ETHER
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-126
2.25e+01 g/L

3.2.6 LogP

1
HANSCH,C ET AL. (1995)
1.00
HANSCH,C ET AL. (1995)

3.2.7 LogS

-0.63
ADME Research, USCD

3.2.8 Stability / Shelf Life

STABLE IN AIR, BUT AFFECTED BY LIGHT
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 66

3.2.9 Decomposition

WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/.
Sax, N.I. Dangerous Properties of Industrial Materials. 6th ed. New York, NY: Van Nostrand Reinhold, 1984., p. 1108

3.2.10 pH

AQ SOLN IS SLIGHTLY ALKALINE TO LITMUS
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 77

3.2.11 Refractive Index

INDEX OF REFRACTION: ALPHA 1.520, GAMMA 1.732
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 293

3.2.12 Caco2 Permeability

-4.44
ADME Research, USCD

3.2.13 Dissociation Constants

pKa
5
SANGSTER (1994)
5.00
Sangster J; LOGKOW Databank. Sangster Res. Lab., Montreal Quebec, Canada (1994)

3.2.14 Collision Cross Section

151.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]

3.2.15 Kovats Retention Index

Standard non-polar
1877 , 1879 , 1880 , 1905 , 1925 , 1950 , 1917 , 1900 , 1903 , 1890 , 1935 , 1940 , 1915 , 1950 , 1903 , 1909.2 , 1890 , 1916
Semi-standard non-polar
1889.8

3.2.16 Other Experimental Properties

FORMS EUTECTIC MIXT WITH ACETYLSALICYLIC ACID, PHENYL SALICYLATE, PHENOL, & CITRIC, TARTARIC & SALICYLIC ACIDS
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1053

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Drugs

Pharmaceuticals -> Metabolite of Metamizole
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.4.1.1 Human Drugs
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra
NMR: 615 (Varian Associates NMR Spectra Catalogue)

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Varian A-60
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
MCB Manufacturing Chemists, Norwood, Ohio
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Varian HA-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 12
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

231.0 99.99

56.0 92

97.0 71

111.0 37

232.0 28

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Notes
instrument=HITACHI RMU-6E
2 of 12
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

56.0 99.99

97.0 35.90

42.0 12.90

111.0 11.90

77.0 8.40

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Notes
instrument=Unknown

4.2.2 MS-MS

1 of 7
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

58.0651 100

56.0495 94.49

97.076 94.07

70.0651 47.67

72.0807 26.85

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2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

58.0651 100

56.0495 83.97

97.0761 80.51

70.0651 57.28

98.0839 46.92

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4.2.3 LC-MS

1 of 57
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
4.881 min
Precursor m/z
232.1444
Precursor Adduct
[M+H]+
Top 5 Peaks

232.1442 999

233.1468 156

187.0852 34

139.0854 20

159.09 15

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License
CC BY
2 of 57
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
4.933 min
Precursor m/z
232.1444
Precursor Adduct
[M+H]+
Top 5 Peaks

232.1438 999

177.101 723

159.0902 582

187.0851 300

149.1059 284

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License
CC BY

4.2.4 Other MS

1 of 3
View All
Other MS
MASS: 1563 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
2 of 3
View All
Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
HITACHI RMU-6E
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

231 999

56 920

97 710

111 370

232 280

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License
CC BY-NC-SA

4.3 UV Spectra

MAX ABSORPTION (0.1 N HCL): 224 NM (A= 409, 1%, 1 CM)
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 825
MAX ABSORPTION (0.1 N NAOH): 226 NM, 263 NM
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 815
UV: 2547 (Sadtler Research Laboratories Spectral Collection)
Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I and II. Boca Raton, FL: CRC Press Inc. 1985., p. V1 111

4.3.1 UV-VIS Spectra

1 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

IR Spectra
IR: 8478 (Sadtler Research Laboratories IR Grating Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
D139106
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Inc.
Catalog Number
D8015
Lot Number
19K1096
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/32992>32992</a>
Lot Number
0612877-5
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Matheson Coleman & Bell
Catalog Number
6847
Lot Number
AX1175
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/32992>32992</a>
Lot Number
0612877-5
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Other Spectra

Intense mass spectral peaks: 56 m/z, 97 m/z, 123 m/z, 231 m/z
Pfleger, K., H. Maurer and A. Weber. Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Parts I and II. Mass Spectra Indexes. Weinheim, Federal Republic of Germany. 1985., p. 373

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Formerly widely used as an antipyretic and analgesic in rheumatism, neuritis, and common colds. Currently used to measure total body water.

7.2 Drug Transformations

Aminopyrine has known transformation products that include 4-Aminoantipyrine, 4-Acetamidoantipyrine, 4-Formylaminoantipyrine, and AMDOPH.
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

7.3 Therapeutic Uses

Anti-Inflammatory Agents, Non-Steroidal
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
IN SOME CASES OF PROLONGED INTRACTABLE FEVER, AS IN HODGKIN'S DISEASE & PERIARTERITIS NODOSA, AMINOPYRINE IS CAPABLE OF CONTROLLING /FEVER/ & MAY BE JUSTIFIED. /SRP: EFFECTIVE AND PREVIOUSLY USED IN THE US AS AN ANTIPYRETIC, ANALGESIC AND ANTI-INFLAMMATORY AGENT/.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 348
ANALGESIC & ANTIPYRETIC. IT IS EFFECTIVE IN RELIEF OF PAIN IN NEURALGIA, DYSMENORRHEA, RHEUMATISM, & SIMILAR PAINFUL CONDITIONS. ...
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1053
MEDICATION (VET): ANALGESIC, ANTIPYRETIC. TO RELIEVE MINOR ACHES, JOINT & MUSCULAR PAINS, & REDUCE ELEVATED TEMP. RELIEVES PAIN & POSSIBLE TOXIC EFFECTS IN INDIGESTIONS OF CATTLE.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 14
For more Therapeutic Uses (Complete) data for AMINOPYRINE (7 total), please visit the HSDB record page.

7.4 Drug Warnings

IF USED AT ALL IN TREATMENT OF INTRACTABLE FEVER, AMINOPYRINE...SHOULD BE EMPLOYED ONLY AFTER SAFER DRUGS & OTHER MEASURES HAVE PROVEN INEFFECTIVE, & ONLY WITH PROPER SUPERVISION & MONITORING.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 348
LEUKOCYTE COUNT & DIFFERENTIAL SHOULD BE CHECKED DURING ADMIN OF LARGE DOSES OR CONTINUED USE OF SMALL DOSES.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1053
IN RARE INDIVIDUALS, INSTEAD OF FRANK AGRANULOCYTOSIS, EACH ADMIN OF AMINOPYRINE PRODUCES SHARP FALL IN TOTAL LEUKOCYTE COUNT ASSOC WITH SEVERE CHILL, SPIKING FEVER, HEADACHE, & PAIN IN MUSCLES & JOINTS; ATTACK IS OVER WITHIN FEW HR.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 347
VET: MAY STIMULATE METABOLISM OF OTHER DRUGS (CHLORINATED HYDROCARBONS, BARBITURATES, PHENYLBUTAZONE, MEPROBAMATE) BY LIVER MICROSOMES.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 14
For more Drug Warnings (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page.

7.5 Reported Fatal Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-239

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Aminophenazone exhibits analgesic, anti-inflammatory, and antipyretic properties.

8.2 ATC Code

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

N - Nervous system

N02 - Analgesics

N02B - Other analgesics and antipyretics

N02BB - Pyrazolones

N02BB03 - Aminophenazone

8.3 Absorption, Distribution and Excretion

IT IS ABSORBED RAPIDLY FOLLOWING ORAL ADMIN...EXCRETED IN URINE UNCHANGED OR CONJUGATED WITH GLUCURONIC & SULFURIC ACIDS.
Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 363
...SLIGHTLY BOUND TO PLASMA PROTEIN...
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 347
THREE METABOLITES OF AMINOPYRINE WERE DETECTED IN THE URINE, SERUM, AND SALIVA OF HEALTH SUBJECTS AFTER INGESTION OF AMINOPYRINE.
WERNER M, WERNER D; AGENTS ACTIONS SUPPL AAS 10 (TRENDS INFLAMMATION RES 2): 99 (1982)
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.
BRITTEBO EB; ACTA PHARMACOL TOXICOL 51 (3): 227 (1982)

8.4 Metabolism / Metabolites

...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.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 186
...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...
Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 165
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.
Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. 67
AMINOPHENAZONE AND ITS METABOLITES; 4-AMINOANTIPYRINE, N-ACETYLAMINOANTIPYRINE AND 4-FORMYLAMINOANTIPYRINE WERE DETECTED IN STUDIES ON HEALTHY SUBJECTS.
WERNER M, WERNER D; AGENTS ACTIONS SUPPL, AAS 10 (TRENDS INFLAMMATION RES 2): 99 (1982)

8.5 Mechanism of Action

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.
Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 93

8.6 Human Metabolite Information

8.6.1 Cellular Locations

Membrane

8.7 Transformations

9 Use and Manufacturing

9.1 Uses

MEDICATION (VET)
MEDICATION

9.1.1 Use Classification

Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
Pharmaceuticals -> Nervous System -> Analgesics -> Pyrazolones
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

9.2 Methods of Manufacturing

PREPD 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
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 66

9.3 Consumption Patterns

ESSENTIALLY 100% AS A MEDICINAL (1976)
SRI

9.4 U.S. Imports

(1972) 1.5X10+6 GRAMS (PRINCPL CUSTMS DISTS)
SRI
(1975) 6.51X10+5 GRAMS (PRINCPL CUSTMS DISTS)
SRI

9.5 General Manufacturing Information

EPA TSCA Commercial Activity Status
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.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 348
INCOMPATIBILITIES: IS INCOMPATIBLE WITH MANY ALKALOIDAL PRECIPITANTS, OXIDIZING AGENTS & MERCURY SALTS...
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1053
CRYSTAL AMIDOPHEN UV IRRADIATED FOR 300 HR CHANGED TO AN ORANGE-BROWN PRODUCT FROM WHICH 3 YELLOW DEGRADATION PRODUCTS WERE ISOLATED.
YANKOVA M, YANKOV L; FARMATSIYA (SOFIA) 32 (4): 5 (1982)
THE PERMEATION OF AMINOPYRINE THROUGH AN ARTIFICIAL INTESTINAL MEMBRANE WAS HIGHER THAN THAT THROUGH AN ARTIFICIAL GASTRIC MEMBRANE.
SUGAWARA K ET AL; BYOIN YAKUGAKU 8 (4): 237 (1982)
THE TRANSFER RATE OF BARBITAL FROM AQUEOUS TO BENZENE PHASE WAS ACCELERATED BY THE ADDITION OF AMINOPYRINE.
KIRYU S ET AL; YAKUGAKU ZASSHI 102 (FEB): 207 (1982)

10 Identification

10.1 Analytic Laboratory Methods

MICROCHEMICAL
Association of Official Analytical Chemists. Official Methods of Analysis. 10th ed. and supplements. Washington, DC: Association of Official Analytical Chemists, 1965. New editions through 13th ed. plus supplements, 1982., p. 13/674 36.102
TITRATION METHOD OF ANALYSIS FOR THE ANALGESIC AMINOPYRINE.
ZOLTAI-MATOLCSY E, SZABO-AKOS Z; ACTA PHARM HUNG 50 (3): 82 (1980)
SPECTROPHOTOMETRY FOLLOWING OXIDATION IN AN ALKALINE MEDIUM.
SZASZ G ET AL; ACTA PHARM HUNG 48 (SEPT): 221 (1978)
AMINOPYRINE WAS SEPARATED BY THIN LAYER CHROMATOGRAPHY & ANALYZED SPECTROPHOTOMETRICALLY FOLLOWING ITS REACTION WITH BROMOCRESOL GREEN.
RADULOVIC D, BLAGOJEVIC Z; ARH FARM 31 (1-2): 17 (1981)

10.2 Clinical Laboratory Methods

AN IMPROVED METHOD OF DETERMINING PHENAZONE DERIVATIVES IN HUMAN PLASMA BY GAS CHROMATOGRAPHIC TECHNIQUES.
SIOUFI A, COULUSSI D; J CHROMATOGR 146 (3): 503 (1978)
NEW, RAPID GAS CHROMATOGRAPHIC METHOD DESCRIBED FOR DETECTION OF BASIC DRUGS IN POSTMORTEM BLOOD.
PIERCE WO ET AL; J ANAL TOXICOL 2 (1): 26 (1978)
A RAPID, SENSITIVE, & SIMPLE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY METHOD IS DESCRIBED FOR THE DIRECT ANALYSIS OF AMINOPYRINE IN SALIVA.
MOLDOWAN MJ; PHARMACOLOGY 26 (6): 331 (1983)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Signal
Danger
GHS Hazard Statements

H301 (96.4%): Toxic if swallowed [Danger Acute toxicity, oral]

H315 (89.3%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (89.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (87.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

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

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 56 reports by companies from 8 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.

11.1.2 Hazard Classes and Categories

Acute Tox. 3 (96.4%)

Skin Irrit. 2 (89.3%)

Eye Irrit. 2 (89.3%)

STOT SE 3 (87.5%)

11.1.3 Health Hazards

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)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.1.4 Fire Hazards

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.2 First Aid Measures

11.2.1 First Aid

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 area; take 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 used; if 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)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.4 Accidental Release Measures

11.4.1 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 directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

11.4.2 Disposal Methods

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.

11.4.3 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.

11.5 Handling and Storage

11.5.1 Nonfire Spill Response

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)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.5.2 Storage Conditions

...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.
Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand Reinhold, 1975., p. 385

11.6 Exposure Control and Personal Protection

11.6.1 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)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.7 Stability and Reactivity

11.7.1 Air and Water Reactions

Water soluble.

11.7.2 Reactive Group

Amides and Imides

Amines, Phosphines, and Pyridines

Hydrocarbons, Aliphatic Unsaturated

11.7.3 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)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.8 Transport Information

11.8.1 DOT Label

Poison

11.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
New Zealand EPA Inventory of Chemical Status
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.

11.9.1 FDA Requirements

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).
21 CFR 200-299, 300-499, 820, and 860 (4/1/93)

11.10 Other Safety Information

Chemical Assessment

IMAP assessments - 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment

IMAP assessments - 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-: Human health tier I assessment

12 Toxicity

12.1 Toxicological Information

12.1.1 Acute Effects

12.1.2 Interactions

ELEVATED URINARY LEVELS OF GLUCARIC ACID...OBSERVED IN RAT & GUINEA PIG FOLLOWING...AMINOPYRINE PRETREATMENT... SIMILARLY, PRETREATMENT OF HUMAN SUBJECTS...INCR URINARY...EXCRETIONS...
Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 349
.../TETRAHYDROCANNABINOL/ INHIBITED MICROSOMAL OXIDN OF AMINOPYRINE...
The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 628
/FENFLURAMINE/ HAS BEEN SHOWN TO INHIBIT THE METABOLISM OF AMINOPYRINE...AND TO DECREASE THE DISTRIBUTION VOLUME OF ANTIPYRINE IN RATS.
The Royal Society of Chemistry. Foreign Compound Metabolism in Mammals. Volume 6: A Review of the Literature Published during 1978 and 1979. London: The Royal Society of Chemistry, 1981., p. 45
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.
BAST A, NOORDHOEK J; PHARM WEEKBL 117 (39): 909 (1982)
For more Interactions (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page.

12.1.3 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.
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-239
THERE IS SEVERE INFLAMMATION OF THROAT OFTEN LEADING TO SLOUGHING, FEVER, MALAISE OR PROSTRATION, & MARKED LEUKOPENIA.
Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 81
CASE HISTORY OF FEMALE PATIENT WITH CHEMICALLY INDUCED AGRANULOCYTOSIS.
GUALDE N, MALINVAUD G; CLIN IMMUNOL IMMUNOPATHOL 24 (2): 220 (1982)
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.
PIFFERI G; BOLL CHIM FARM 120 (JULY): 373 (1981)
For more Human Toxicity Excerpts (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page.

12.1.4 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.
Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 363
AMINOPYRINE WAS AMONG COMPOUNDS PRODUCING CHROMOSOME ABERRATIONS AND SISTER CHROMATID EXCHANGES IN CHINESE HAMSTER CELLS.
ABE S, SASAKI M; J NATL CANCER INST 58: 1635 (1977)
...NO DELETERIOUS EFFECTS IN PREGNANT RATS (150 MG/KG), RABBITS (90 MG/KG) & MICE (180 MG/KG) TREATED DAILY DURING MOST OF THEIR GESTATION.
Shepard, T. H. Catalog of Teratogenic Agents. 3rd ed. Baltimore, MD.: Johns Hopkins University Press, 1980., p. 18
...FOUND THAT AMINOPYRINE CAUSED EXCITEMENT, INCOORDINATION AND MUSCULAR WEAKNESS IN CATTLE...TOXICITY DUE TO FORMALDEHYDE LIBERATED AS THE DRUG WAS METABOLIZED.
Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 93
For more Non-Human Toxicity Excerpts (Complete) data for AMINOPYRINE (6 total), please visit the HSDB record page.

12.2 Ecological Information

12.2.1 Body Burden

AMINOPYRINE WAS DETECTED IN THE BONE OF A MALE JAPANESE SKELETON AT 12.8 UG/G.
TERAZAWA K, TAKATORI T; J FORENSIC SCI 27 (4): 844 (1982)

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

16.2 Drug-Drug Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 KEGG: ATC

18.5 KEGG: Drug Groups

18.6 WHO ATC Classification System

18.7 ChemIDplus

18.8 CAMEO Chemicals

18.9 ChEMBL Target Tree

18.10 UN GHS Classification

18.11 NORMAN Suspect List Exchange Classification

18.12 CCSBase Classification

18.13 EPA DSSTox Classification

18.14 EPA TSCA and CDR Classification

18.15 EPA Substance Registry Services Tree

18.16 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://services.industrialchemicals.gov.au/search-assessments/
    3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  6. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. EPA Chemicals under the TSCA
    3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  10. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. Hazardous Substances Data Bank (HSDB)
  12. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  13. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  14. ChEBI
  15. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  16. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  17. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  18. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  19. IUPAC Digitized pKa Dataset
    pyrazole, 4-dimethylamino-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-
    https://github.com/IUPAC/Dissociation-Constants
  20. MassBank Europe
  21. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  22. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  23. SpectraBase
  24. Japan Chemical Substance Dictionary (Nikkaji)
  25. KEGG
    LICENSE
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  26. Metabolomics Workbench
  27. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  28. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    4-Dimethylaminoantipyrine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  29. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
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    https://www.whocc.no/copyright_disclaimer/
  30. PharmGKB
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  31. Pharos
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    https://pharos.nih.gov/about
  32. Springer Nature
  33. SpringerMaterials
    3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://materials.springer.com/substanceprofile/docs/smsid_bgzaosfhsvvzoyjt
  34. Thieme Chemistry
    LICENSE
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  36. Wikipedia
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  38. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  39. PubChem
  40. GHS Classification (UNECE)
  41. EPA Substance Registry Services
  42. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  43. PATENTSCOPE (WIPO)
  44. NCBI
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