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4-Aminoantipyrine

PubChem CID
2151
Structure
4-Aminoantipyrine_small.png
4-Aminoantipyrine_3D_Structure.png
4-Aminoantipyrine__Crystal_Structure.png
Molecular Formula
Synonyms
  • 4-Aminoantipyrine
  • AMPYRONE
  • 83-07-8
  • 4-Aminophenazone
  • Metapirazone
Molecular Weight
203.24 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
4-aminoantipyrine is a pyrazolone, a member of the class of pyrazoles that is antipyrine substituted at C-4 by an amino group. It is a metabolite of aminopyrine and of metamizole. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antirheumatic drug, a peripheral nervous system drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antipyretic, a drug metabolite and a marine xenobiotic metabolite. It is a primary amino compound and a pyrazolone. It is functionally related to an antipyrine.
A metabolite of AMINOPYRINE with analgesic and anti-inflammatory properties. It is used as a reagent for biochemical reactions producing peroxides or phenols. Ampyrone stimulates LIVER MICROSOMES and is also used to measure extracellular water.
See also: Aminopyrine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Aminoantipyrine.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 3
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-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/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RLFWWDJHLFCNIJ-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
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H13N3O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

83-07-8

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 NSC Number

2.3.11 PharmGKB ID

2.3.12 Wikidata

2.3.13 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4 Amino 1,5 Dimethyl 2 Phenyl 3H Pyrazolone
  • 4 Aminoantipyrine
  • 4 Aminophenazone
  • 4-Amino-1,5-Dimethyl-2-Phenyl-3H-Pyrazolone
  • 4-Aminoantipyrine
  • 4-Aminophenazone
  • Aminoantipyrine
  • Ampyrone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
203.24 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
203.105862047 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
203.105862047 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
49.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
305
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 Dissociation Constants

3.2.2 Collision Cross Section

151.49 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

154.44 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

135.51 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

141.76 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
142.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

156.8 Ų [M+Na]+

142.48 Ų [M+H]+

S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.2.3 Kovats Retention Index

Standard non-polar
1957 , 1950

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Metabolite of Metamizole
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
3.3.1.1 Animal Drugs
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

3.3.2 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Maybridge Chemical Company Ltd., North Cornwall, England
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 10
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Unknown
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

56 99.99

84 64.90

57 63.90

203 43.90

83 26.90

Thumbnail
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License
CC BY-NC-SA
2 of 10
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
JEOL JMS-D-3000
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

56 99.99

57 66.11

84 56.33

203 55.58

42 27.71

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License
CC BY-NC-SA

4.2.2 MS-MS

1 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

56.0499 100

94.066 47.85

77.039 25.03

83.061 21.12

104.0499 13.51

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2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

56.0499 100

94.066 47.89

77.039 25.04

83.061 21.09

104.0499 13.48

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4.2.3 LC-MS

1 of 58
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Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
4.783 min
Precursor m/z
204.1131
Precursor Adduct
[M+H]+
Top 5 Peaks

56.0498 999

94.0653 247

83.0605 138

159.0917 130

104.0493 77

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License
dl-de/by-2-0
2 of 58
View All
Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
70
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
4.783 min
Precursor m/z
204.1131
Precursor Adduct
[M+H]+
Top 5 Peaks

56.0499 999

77.039 441

51.0232 116

42.0343 54

83.0602 50

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License
dl-de/by-2-0

4.2.4 Other MS

1 of 5
View All
Authors
KOGA M, UNIV. OF OCCUPATIONAL AND ENVIRONMENTAL HEALTH
Instrument
VARIAN MAT-44
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

56 999

57 720

84 590

83 372

203 287

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 5
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

56 999

203 930

57 830

84 830

42 620

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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 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.
Thumbnail
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2 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Source of Sample
Carl Roth GmbH & Co Chem. Fabrik Karlsruhe
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II) ground
Source of Spectrum
Forensic Spectral Research
Source of Sample
Matheson, Coleman & Bell
Catalog Number
AX815
Lot Number
3H28
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Sample
Aldrich
Catalog Number
A39300
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 Raman Spectra

1 of 2
Instrument Name
Thermo Nicolet FT-Raman 960
Technique
FT-Raman
Source of Sample
Fisher Scientific International, Inc.
Copyright
Copyright © 2003-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Matheson Coleman & Bell
Catalog Number
AX815
Lot Number
3H28477
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Transformations

4-Aminoantipyrine is a known transformation product of 4-Formylaminoantipyrine, 4-Acetamidoantipyrine, and Aminopyrine.
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Indicators and Reagents
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)
Anti-Inflammatory Agents, Non-Steroidal
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

8.2 ATC Code

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

8.3 Transformations

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

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

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 99% (103 of 104) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1% (1 of 104) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (99%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (90.4%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (92.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (88.5%): 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+P317, 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 104 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 104 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 11 notifications provided by 103 of 104 reports by companies with hazard statement code(s).

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.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (99%)

Skin Irrit. 2 (90.4%)

Eye Irrit. 2 (92.3%)

STOT SE 3 (88.5%)

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Does not have an individual approval but may be used under an appropriate group standard

10.3 Other Safety Information

Chemical Assessment

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

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

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 ChEMBL Target Tree

16.5 UN GHS Classification

16.6 NORMAN Suspect List Exchange Classification

16.7 CCSBase Classification

16.8 EPA DSSTox Classification

16.9 EPA TSCA and CDR Classification

16.10 EPA Substance Registry Services Tree

16.11 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. 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/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. 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
  5. EPA Chemicals under the TSCA
    3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
    4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one (EC: 201-452-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/87681
  8. 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
  9. 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/
  10. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  11. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  12. 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-Aminoantipyrine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  13. ChEBI
  14. 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
  15. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  16. The Cambridge Structural Database
  17. 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
  18. 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
  19. IUPAC Digitized pKa Dataset
    pyrazole, 4-amino-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-
    https://github.com/IUPAC/Dissociation-Constants
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. MassBank Europe
  22. 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
  23. SpectraBase
    3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-
    https://spectrabase.com/spectrum/G16VkHJD4ZE
  24. Metabolomics Workbench
  25. NMRShiftDB
  26. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  27. Springer Nature
  28. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  29. Wikidata
  30. Wikipedia
  31. Wiley
  32. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Anti-Inflammatory Agents, Non-Steroidal
    https://www.ncbi.nlm.nih.gov/mesh/68000894
  33. PubChem
  34. GHS Classification (UNECE)
  35. EPA Substance Registry Services
  36. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  37. PATENTSCOPE (WIPO)
CONTENTS