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Carboxyprimaquine

PubChem CID
127542
Structure
Carboxyprimaquine_small.png
Carboxyprimaquine_3D_Structure.png
Molecular Formula
Synonyms
  • 77229-68-6
  • Carboxyprimaquine
  • 4-((6-Methoxyquinolin-8-yl)amino)pentanoic acid
  • 4-[(6-methoxyquinolin-8-yl)amino]pentanoic acid
  • Carboxy Primaquine
Molecular Weight
274.31 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
Carboxyprimaquine is an organonitrogen compound and an organooxygen compound. It is functionally related to a gamma-amino acid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Carboxyprimaquine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(6-methoxyquinolin-8-yl)amino]pentanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C15H18N2O3/c1-10(5-6-14(18)19)17-13-9-12(20-2)8-11-4-3-7-16-15(11)13/h3-4,7-10,17H,5-6H2,1-2H3,(H,18,19)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

KIMKJIXTIWKABF-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC(CCC(=O)O)NC1=C2C(=CC(=C1)OC)C=CC=N2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H18N2O3
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

77229-68-6

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 HMDB ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 PharmGKB ID

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 8-(3-carboxy-1-methylpropylamino)-6-methoxyquinoline
  • carboxyprimaquine
  • CMPAMOQ

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
274.31 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
2.4
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
274.13174244 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
274.13174244 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
71.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
324
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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
1
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)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

NIST Number
128319
Library
Main library
Total Peaks
150
m/z Top Peak
201
m/z 2nd Highest
274
m/z 3rd Highest
215
Thumbnail
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4.1.2 MS-MS

1 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

132.0681 100

55.0543 54.58

160.063 19.05

175.0863 16.01

131.0603 14.11

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2 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

55.0542 100

175.0865 97.67

132.0682 78.24

160.0631 44.61

83.0491 29.99

Thumbnail
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4.1.3 LC-MS

1 of 9
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Authors
R. Gulde, E. Schymanski, K. Fenner, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 (nominal)
Fragmentation Mode
HCD
Column Name
Atlantis T3 3um, 3.0x150mm, Waters with guard column
Retention Time
16.8 min
Precursor m/z
275.139
Precursor Adduct
[M+H]+
Top 5 Peaks

257.1284 999

187.0962 36

60.0808 26

83.0855 19

57.0699 16

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License
CC BY
Reference
Gulde, R.; Meier, U.; Schymanski, E. L.; Kohler, H.-P. E.; Helbling, D. E.; Derrer, S.; Rentsch, D.; Fenner, K. Systematic Exploration of Biotransformation Reactions of Amine-Containing Micropollutants in Activated Sludge. Environmental Science & Technology 2016, 50 (6), 2908-20. DOI:10.1021/acs.est.5b05186
2 of 9
View All
Authors
R. Gulde, E. Schymanski, K. Fenner, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 (nominal)
Fragmentation Mode
HCD
Column Name
Atlantis T3 3um, 3.0x150mm, Waters with guard column
Retention Time
16.8 min
Precursor m/z
275.139
Precursor Adduct
[M+H]+
Top 5 Peaks

257.1284 999

175.0866 102

101.0598 71

57.0699 53

83.0856 48

Thumbnail
Thumbnail
License
CC BY
Reference
Gulde, R.; Meier, U.; Schymanski, E. L.; Kohler, H.-P. E.; Helbling, D. E.; Derrer, S.; Rentsch, D.; Fenner, K. Systematic Exploration of Biotransformation Reactions of Amine-Containing Micropollutants in Activated Sludge. Environmental Science & Technology 2016, 50 (6), 2908-20. DOI:10.1021/acs.est.5b05186

6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Springer Nature References

7.4 Chemical Co-Occurrences in Literature

7.5 Chemical-Gene Co-Occurrences in Literature

7.6 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

8.5 Chemical-Gene Co-Occurrences in Patents

9 Classification

9.1 MeSH Tree

9.2 ChEBI Ontology

9.3 ChemIDplus

9.4 NORMAN Suspect List Exchange Classification

9.5 EPA DSSTox Classification

9.6 MolGenie Organic Chemistry Ontology

10 Information Sources

  1. ChEBI
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. 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
  4. EPA DSSTox
    4-[(6-methoxyquinolin-8-yl)amino]pentanoic acid
    https://comptox.epa.gov/dashboard/DTXSID40891676
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
    4-((6-Methoxyquinolin-8-yl)amino)pentanoic acid
    http://www.hmdb.ca/metabolites/HMDB0247386
  6. Japan Chemical Substance Dictionary (Nikkaji)
  7. MassBank Europe
  8. 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
  9. Metabolomics Workbench
  10. 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
  11. 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
  12. Springer Nature
  13. Wikidata
    4-[(6-methoxyquinolin-8-yl)amino]pentanoic acid
    https://www.wikidata.org/wiki/Q82003473
  14. PubChem
  15. 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
    8-(3-carboxy-1-methylpropylamino)-6-methoxyquinoline
    https://www.ncbi.nlm.nih.gov/mesh/67035150
  16. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
CONTENTS