7-Methylxanthine - ≥97% , CAS No.552-62-5

CAS: 552-62-5 Cat. No.: M111858 Molecular Weight: 166.14 Beilstein Registry Number: 171027 EC Number: 209-019-0

GRADE & PURITY ≥97%

Synonyms

2,6-Dihydroxy-7-methylpurine | 7-methyl xanthine | CHEBI:48991 | MFCD00037979 | PDSP2_001024 | 7-Methylxanthine | 7-Methyl-2,6-dioxypurin | BDBM82522 | Heteroxanthin | 7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione | FT-0672370 | 1H-Purine-2, 3,7-dihydro

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

General description：

7-Methylxanthine is an oxopurine, which belongs to the class of xanthines. It may be synthesized by the reaction between 4-amino-1-methylimidazole-5-carboxamide and diethyl carbonate.

description：

7-Methylxanthine can be used as a building block to synthesize tricyclic imidazo[2,1-i]purinone derivatives as potential adenosine receptor antagonists

Specifications

Synonyms

2, 6-Dihydroxy-7-methylpurine | 7-methyl xanthine | CHEBI:48991 | MFCD00037979 | PDSP2_001024 | 7-Methylxanthine | 7-Methyl-2, 6-dioxypurin | BDBM82522 | Heteroxanthin | 7-methyl-2, 3, 6, 7-tetrahydro-1H-purine-2, 6-dione | FT-0672370 | 1H-Purine-2, 3, 7-dihydro

Specifications & Purity

≥97%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504754284
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754284
• Canonical Smiles: CN1C=NC2=C1C(=O)NC(=O)N2
• IUPAC Name: 7-methyl-3H-purine-2,6-dione
• InChIKey: PFWLFWPASULGAN-UHFFFAOYSA-N
• INCHI: 1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)
• Isomeric SMILES: CN1C=NC2=C1C(=O)NC(=O)N2
• WGK Germany: 3
• Molecular Weight: 166.14
• Beilstein: 171027
• Reaxy-Rn: 171027
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=171027&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Imidazopyrimidines
      • Subclass Purines and purine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Imidazopyrimidines
• Subclass: Purines and purine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Xanthines
• Alternative Parents: Alkaloids and derivatives Hydroxypyrimidines N-substituted imidazoles Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthine - Alkaloid or derivatives - Hydroxypyrimidine - Pyrimidine - N-substituted imidazole - Heteroaromatic compound - Imidazole - Azole - Azacycle - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound 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.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GDA Tbio Guanine deaminase (19 Activities)

Discover Target: GDA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Adora2b Adenosine A2 receptor (1828 Activities)

Discover Target: Adora2b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in dimethyl sulfoxide. Insoluble in water.
• Melt Point(°C): ≥300℃
• Molecular Weight: 166.140 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 166.049 Da
• Monoisotopic Mass: 166.049 Da
• Topological Polar Surface Area: 76.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 242.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Fan Yuzhuo, Li Jiarui, Huang Lvzhen, Wang Kai, Zhao Mingwei.  (2022)  7-Methylxanthine Influences the Behavior of ADORA2A-DRD2 Heterodimers in Human Retinal Pigment Epithelial Cells.  OPHTHALMIC RESEARCH,  65  (6): (678-684).  [PMID:35724635] [10.1159/000525563]

2. Dekai Zheng, Changhao Cheng, Yanhua Tang, Zhixin Fang, Xuelian Gao, Yuchuan Chen, Qiuhong You, Kaifeng Wang, Heqi Zhou, Zhixian Lan, Jian Sun.  (2024)  Circulating metabolites are associated with persistent elevations of ALT in patients with chronic hepatitis B with complete viral suppression.  JOURNAL OF MEDICAL VIROLOGY,  96  (6): (e29723).  [PMID:38828911] [10.1002/jmv.29723]

3. Chang Liu, Yinuo Wu, Huizhe Zhao, Xiangyu Gu, Jinyang Gu, Mengmeng Zhao, Shangci Zuo, Pengchao Wang.  (2024)  Highly Efficient Whole-Cell Biocatalysis for the Biosynthesis of 7-Methylxanthine and Other Xanthine Derivatives.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.4c01165]