1,7-Dimethylxanthine (CHEM020553)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 07:13:07 UTC
Update Date2016-11-09 01:16:13 UTC
Accession NumberCHEM020553
Identification
Common Name1,7-Dimethylxanthine
ClassSmall Molecule
DescriptionA dimethylxanthine having the two methyl groups located at positions 1 and 7. It is a metabolite of caffeine and theobromine in animals.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneChEBI
p-XanthineChEBI
1,7-Dimethyl-xanthineHMDB
1,7-DimethylxanthineHMDB, MeSH
Chemical FormulaC7H8N4O2
Average Molecular Mass180.164 g/mol
Monoisotopic Mass180.065 g/mol
CAS Registry Number611-59-6
IUPAC Name1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nameparaxanthine
SMILESCN1C=NC2=C1C(=O)N(C)C(=O)N2
InChI IdentifierInChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChI KeyQUNWUDVFRNGTCO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.13 g/LALOGPS
logP-0.63ALOGPS
logP0.24ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.76ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.72 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-2980000000-6ee5dc3100885f205536Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-2980000000-6ee5dc3100885f205536Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uka-3900000000-d979badf45de391835d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-2d1aa5f80618f452686cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-3326bcbee23b63dcc230Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-9824aef9dc2f13c24bccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00e9-1900000000-9d0dde13bb1ce13e2644Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00fr-0900000000-1aa733a1b7e41b994d8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-1900000000-190ff3302e9f5a37a72fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00fr-0900000000-1aa733a1b7e41b994d8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0900000000-729a2bed81ba15260ffaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0900000000-18d0a9c63a1dfb683c9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-c52421f0ba1f46241853Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-0bd6ed3d764e5a9b374eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-1900000000-9d0dde13bb1ce13e2644Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w29-0940000000-127f99d8e7324e01eb66Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ik9-0930000000-fe234438cbe3be0b30f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1900000000-190ff3302e9f5a37a72fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-d6040ea84fe19d8c5cc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-935e5a47dc1abe7b1196Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-3900000000-2f3998477ce19f3ff96fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-c89111b73e8a9a163111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5e7c398698bb5c16617dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-522eaddc21ef92e70e62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-d10a1141c0e21f56ec00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-bc2d3cb520a4fcb81529Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-e2e2992ce9b1265af790Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05am-9300000000-e1aefedceb8692ffe91fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001860
FooDB IDFDB022714
Phenol Explorer IDNot Available
KNApSAcK IDC00039930
BiGG IDNot Available
BioCyc ID1-7-DIMETHYLXANTHINE
METLIN ID1457
PDB IDNot Available
Wikipedia LinkParaxanthine
Chemspider ID4525
ChEBI ID25858
PubChem Compound ID4687
Kegg Compound IDC13747
YMDB IDNot Available
ECMDB IDM2MDB005812
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10416066
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10572151
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10593655
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10877011
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11090584
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1128545
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12110375
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16870158
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17655324
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18621927
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=20004571
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20614853
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=20853468
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21380987
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=2882985
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=3371146
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=3798364
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=7920690
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=7977734
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=8529334
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=9920286
23. Mueller, Christa E.; Deters, Dirk; Dominik, Andreas; Pawlowski, Maciej. Synthesis of paraxanthine and isoparaxanthine analogs (1,7- and 1,9-substituted xanthine derivatives). Synthesis (1998), (10), 1428-1436.
24. Mueller, Christa E.; Deters, Dirk; Dominik, Andreas; Pawlowski, Maciej. Synthesis of paraxanthine and isoparaxanthine analogs (1,7- and 1,9-substituted xanthine derivatives). Synthesis (1998), (10), 1428-1436.
25. Fuhr U, Rost KL: Simple and reliable CYP1A2 phenotyping by the paraxanthine/caffeine ratio in plasma and in saliva. Pharmacogenetics. 1994 Jun;4(3):109-16.
26. Tanaka E: Simultaneous determination of caffeine and its primary demethylated metabolites in human plasma by high-performance liquid chromatography. J Chromatogr. 1992 Mar 27;575(2):311-4.
27. Horrigan LA, Kelly JP, Connor TJ: Immunomodulatory effects of caffeine: friend or foe? Pharmacol Ther. 2006 Sep;111(3):877-92. Epub 2006 Mar 15.
28. Holstege A, Kurz M, Weinbeck M, Gerok W: Excretion of caffeine and its primary degradation products into bile. J Hepatol. 1993 Jan;17(1):67-73.
29. Granfors MT, Backman JT, Laitila J, Neuvonen PJ: Oral contraceptives containing ethinyl estradiol and gestodene markedly increase plasma concentrations and effects of tizanidine by inhibiting cytochrome P450 1A2. Clin Pharmacol Ther. 2005 Oct;78(4):400-11.
30. Blanchard J, Weber CW, Shearer LE: HPLC analysis of methylxanthines in human breast milk. J Chromatogr Sci. 1990 Dec;28(12):640-2.
31. Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600.
32. Christensen M, Andersson K, Dalen P, Mirghani RA, Muirhead GJ, Nordmark A, Tybring G, Wahlberg A, Yasar U, Bertilsson L: The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. Clin Pharmacol Ther. 2003 Jun;73(6):517-28.
33. Holland DT, Godfredsen KA, Page T, Connor JD: Simple high-performance liquid chromatography method for the simultaneous determination of serum caffeine and paraxanthine following rapid sample preparation. J Chromatogr B Biomed Sci Appl. 1998 Apr 10;707(1-2):105-10.
34. Fuhr U, Rost KL, Engelhardt R, Sachs M, Liermann D, Belloc C, Beaune P, Janezic S, Grant D, Meyer UA, Staib AH: Evaluation of caffeine as a test drug for CYP1A2, NAT2 and CYP2E1 phenotyping in man by in vivo versus in vitro correlations. Pharmacogenetics. 1996 Apr;6(2):159-76.
35. Zaigler M, Rietbrock S, Szymanski J, Dericks-Tan JS, Staib AH, Fuhr U: Variation of CYP1A2-dependent caffeine metabolism during menstrual cycle in healthy women. Int J Clin Pharmacol Ther. 2000 May;38(5):235-44.
36. Blanchard J, Weber CW, Shearer LE: Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. Biopharm Drug Dispos. 1992 Apr;13(3):187-96.
37. Wahllander A, Renner E, Karlaganis G: High-performance liquid chromatographic determination of dimethylxanthine metabolites of caffeine in human plasma. J Chromatogr. 1985 Mar 22;338(2):369-75.
38. Koch JP, ten Tusscher GW, Koppe JG, Guchelaar HJ: Validation of a high-performance liquid chromatography assay for quantification of caffeine and paraxanthine in human serum in the context of CYP1A2 phenotyping. Biomed Chromatogr. 1999 Jun;13(4):309-14.
39. Sachse C, Ruschen S, Dettling M, Schley J, Bauer S, Muller-Oerlinghausen B, Roots I, Brockmoller J: Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism. Clin Pharmacol Ther. 1999 Oct;66(4):431-8.
40. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
41. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.