3-Methylxanthine - 10mM in DMSO , CAS No.1076-22-8

CAS: 1076-22-8 Cat. No.: M420532 Molecular Weight: 166.14 Beilstein Registry Number: 180944 EC Number: 214-058-1

GRADE & PURITY 10mM in DMSO

Synonyms

CCG-39565 | W-108741 | WS6X982OEC | Propanoic acid, 2-oxo-3-(phosphonooxy)- | STK776266 | Z1741977122 | 3,7-Dihydro-3-methyl-1H-purine-2,6-dione | 3,9-dihydro-3-methyl-1H-purine-2,6-dione | 3-Methyl-3,7-dihydro-purine-2,6-dione | 3-methyl-3,7-dihydropurin

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Product Introduction

3-Methylxanthine, a xanthine derivative, is a cyclic guanosine monophosphate (GMP) inhibitor, with an IC50 of 920 μM on guinea-pig isolated trachealis muscle.

Application

3-Methylxanthine is a Xanthine derivative with diuretic, cardiac stimulant and smooth muscle relaxant activities; isomeric with theobromine.They can also act as Bronchodilator.

Specifications

Synonyms

CCG-39565 | W-108741 | WS6X982OEC | Propanoic acid, 2-oxo-3-(phosphonooxy)- | STK776266 | Z1741977122 | 3, 7-Dihydro-3-methyl-1H-purine-2, 6-dione | 3, 9-dihydro-3-methyl-1H-purine-2, 6-dione | 3-Methyl-3, 7-dihydro-purine-2, 6-dione | 3-methyl-3, 7-dihydropurin

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Pubchem Sid: 528759062
• Canonical Smiles: CN1C2=C(C(=O)NC1=O)NC=N2
• IUPAC Name: 3-methyl-7H-purine-2,6-dione
• InChIKey: GMSNIKWWOQHZGF-UHFFFAOYSA-N
• INCHI: 1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)
• Isomeric SMILES: CN1C2=C(C(=O)NC1=O)NC=N2
• WGK Germany: 1
• RTECS: ZD8750000
• Molecular Weight: 166.14
• Beilstein: 180944
• Reaxy-Rn: 180944
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=180944&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: Purinones Alkaloids and derivatives Pyrimidones Hydroxypyrimidines Imidazoles Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthine - Purinone - Alkaloid or derivatives - Pyrimidone - Hydroxypyrimidine - Pyrimidine - Heteroaromatic compound - Imidazole - Azole - Azacycle - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxide - 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

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

Discover Target: ADORA2A

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

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

PDE4A Tclin Phosphodiesterase 4 (3344 Activities)

Discover Target: PDE4A

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

Associated Targets(non-human)

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

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

Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 360°C(dec.)(lit.)
• Molecular Weight: 166.140 g/mol
• XLogP3: -0.700
• 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: 78.100 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. Hansen Yang, Zhimiao Wang, Hualiang An, Qiusheng Yang, Wei Xue, Fang Li, Yanji Wang.  (2022)  Catalyst-free N-methylation of 3-methylxanthine with dimethyl carbonate in water: green synthesis of theobromine.  NEW JOURNAL OF CHEMISTRY,  46  (27): (12934-12940).  [PMID:] [10.1039/D2NJ01624A]