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Xanthinol

PubChem CID
9913
Structure
Xanthinol_small.png
Xanthinol_3D_Structure.png
Molecular Formula
Synonyms
  • Xanthinol
  • 2530-97-4
  • xantinol
  • UNII-TN1B5910V2
  • 7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione
Molecular Weight
311.34 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-27
Description
7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione is an oxopurine.
Xanthinol is a very potent water-soluble derivative of niacin that can be found in diet supplements. It is also known as xanthinol nicotinate. Xaninthol is known to be a potent vasodilator that can easily pass through the cell membrane and once inside the cell it causes an increase in glucose metabolism resulting in an increased energy. It was approved as a drug in 1998 in Canada and nowadays its status is cancelled post marketing.
XANTHINOL is a small molecule drug with a maximum clinical trial phase of IV and is indicated for cardiovascular disease.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Xanthinol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C13H21N5O4/c1-15(4-5-19)6-9(20)7-18-8-14-11-10(18)12(21)17(3)13(22)16(11)2/h8-9,19-20H,4-7H2,1-3H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

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

2.1.4 SMILES

CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC(CN(C)CCO)O
Computed by OEChem 2.3.0 (PubChem release 2024.11.20)

2.2 Molecular Formula

C13H21N5O4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2530-97-4

2.3.2 Deprecated CAS

117030-05-4, 59496-54-7

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

Jupal

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
311.34 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
-1.8
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
6
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
311.15935417 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
311.15935417 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
102Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
435
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)

3.2 Experimental Properties

3.2.1 Boiling Point

589.3ºC at 760 mmHg
'MSDS'

3.2.2 Melting Point

179-180 ºC
'MSDS'

3.2.3 Solubility

<1 mg/mL
'MSDS'

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 3
View All
NIST Number
246791
Library
Main library
Total Peaks
52
m/z Top Peak
88
m/z 2nd Highest
44
m/z 3rd Highest
42
Thumbnail
Thumbnail
2 of 3
View All
Source of Spectrum
Mass Spectrometry Committee of the Toxicology Section of the American Academy of Forensic Sciences
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. Portions provided by AAFS, Toxicology Section. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 MS-MS

Spectra ID
Ionization Mode
Positive
Top 5 Peaks

312.16785 100

132.10197 71.53

237.09862 65.45

114.09274 64.67

219.08842 37.70

Thumbnail
Thumbnail

4.1.3 LC-MS

1 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
312.166
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
positive
Collision Energy
HCD (NCE 20-30-40%)
Retention Time
6.013233
Top 5 Peaks

312.16602 100

132.10188 30.83

114.09158 26.75

237.09792 24.15

219.08739 13.62

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
312.167
Instrument
SCIEX TripleTOF 6600
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
35 eV
Retention Time
5.7772
Top 5 Peaks

312.16785 100

132.10197 71.53

237.09862 65.45

114.09274 64.67

219.08842 37.70

Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Xanthinol is primarily used in diet supplements to increase the brain metabolism of glucose and obtain ATP. Xanthinol is also used as an agent to reduced cholesterol as it is a vasodilator. Its action allows having an elevated rate of blood flow in the brain which helps improve memory function, concentration and awareness. Thus, due to his actions, xanthinol is indicated to improve cerebrovascular and peripheral vascular disorders as well as hyperlipidaemias.

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Reports indicate that xanthinol increases blood flow in the vascular beds. The use of xanthinol in clinical trials have reported improvements in the performance of healthy elderly individuals in short- and long-term memory tests. The later effect is explained by the enhancing on the cell metabolism and oxygen supply in the brain by the rise of ATP in erythrocytes which allows penetration into capillaries easier and a higher oxygen pressure in the capillary blood which improves oxygenation of surrounding tissue.

8.2 Absorption, Distribution and Excretion

Absorption
Xanthinol is readily absorbed in the body with an absorption half life of 0.4 h. After absorption, xanthinol nicotinate rapidly degardes into the negatively charged nicotinic acid and the positively charged xanthinol ion.
Route of Elimination
In urine, the two stereoisomeric forms of the xanthinol metabolites represents about 7-8% of the eliminated xanthinol.
Volume of Distribution
The volume of distribution of xanthinol is 0.93 L/kg.
Clearance
The total body clearance rate for xanthinol is 0.63 L h/kg.

8.3 Metabolism / Metabolites

As part of the metabolism of xanthinol, there is a formation of two metabolites that correspond to stereoisomeric forms of 2-coffeinyl-N-methyl-6-hydroxy-morpholines. These metabolites can be described structurally as semiacetals of a terminal aldehyde formed from xanthinol.

8.4 Biological Half-Life

The reported elimination half-life of xanthinol is 1.67h.

8.5 Mechanism of Action

The positively charged xanthinol ion is thought to help the transportation of the nicotinic acid into the cell since the later cannot freely diffuse through the cell membrane. The mechanism of action is thought to be related to present influence in the cell metabolism through the nucleotides NAD and NADP. Also, the nicotinic acid is a coenzyme for a lot of proteins involved in tissue respiration (Embden-Meyerhof and citrate cycle). The effect of xanthinol nicotinate causes an increase in glucose metabolism and energy gain.

9 Safety and Hazards

9.1 Other Safety Information

Chemical Assessment

IMAP assessments - 1H-Purine-2,6-dione, 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-: Environment tier I assessment

IMAP assessments - 1H-Purine-2,6-dione, 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-: Human health tier I assessment

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

10.1.2 Protein Binding

From the administered dose of xanthinol between 90.9 and 100% can be retreived in the plasma.

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 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

14.2 Drug-Drug Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 NORMAN Suspect List Exchange Classification

16.5 EPA DSSTox Classification

16.6 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1H-Purine-2,6-dione, 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-
    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. 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
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. ChEBI
    7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:94314
  8. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  9. 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
  10. 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
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. 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
  13. Metabolomics Workbench
  14. 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
    Theophylline, 7-(2-hydroxy-3-(N-(2-hydroxyethyl)-N-methylamino)propyl)-
    http://www.nist.gov/srd/nist1a.cfm
  15. SpectraBase
    7-(2-Hydroxy-3-[(2-hydroxyethyl)(methyl)amino]propyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
    https://spectrabase.com/spectrum/Ga4ZLRHDf4X
  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/
    XANTINOL NICOTINATE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. Springer Nature
  18. 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/
  19. Wikidata
  20. Wikipedia
  21. PubChem
  22. 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
  23. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  24. PATENTSCOPE (WIPO)
CONTENTS