Xanthinol
Basic information
- CAS
2530-97-4- Standard SMILES
CN(CCO)CC(O)Cn1cnc2c1c(=O)n(C)c(=O)n2C- InChIKey
DSFGXPJYDCSWTA-UHFFFAOYSA-N- Molecular formula
- C13H21N5O4
- Average molar mass
- 311.34 g/mol
- Monoisotopic mass
- 311.15935417
Overview
7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione is an oxopurine.
Names & identifiers
- Preferred name
- Xanthinol
- IUPAC
- 7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione
- English name
- Xanthinol
- Molecular formula
- C13H21N5O4
- Molecular weight
- 311.34
Names & synonyms
Xanthinol2530-97-4xantinolUNII-TN1B5910V2TN1B5910V27-(2-Hydroxy-3-(N-(2-hydroxyethyl)-N-methylamino)propyl)theophyllineDTXSID1048255Theophylline, 7-(2-hydroxy-3-(N-(2-hydroxyethyl)-N-methylamino)propyl)-7-{2-hydroxy-3-[(2-hydroxyethyl)(methyl)amino]propyl}-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione7-(2-hydroxy-3-((2-hydroxyethyl)(methyl)amino)propyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dioneRefChem:195113DTXCID6028230
Show more names
7-[2-Hydroxy-3-[N-(2-hydroxyethyl)-N-methylamino]propyl]theophyline7-[2-Hydroxy-3-[N-(2-hydroxyethyl)-N-methylamino]propyl]-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione1,3-Dimethyl-3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1H-purine-2,6-dione1H-Purine-2,6-dione, 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-
DSFGXPJYDCSWTA-UHFFFAOYSA-N7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione7-{2-hydroxy-3-[(2-hydroxyethyl)(methyl)amino]propyl}-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dioneJupal7-(2-hydroxy-3-((2-hydroxyethyl)(methyl)amino)propyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dioneXanintholSCHEMBL121656orb3028211
Database identifiers
- CAS
2530-97-4- PubChem CID
- 9913
- DTXSID
DTXSID1048255- ChEMBL
CHEMBL1624126- ChEBI
CHEBI:94314- UNII
- TN1B5910V2
- Nikkaji
- J7.603A
Properties
Computed structural properties
- XLogP
- -1.8
- Topological polar surface area
- 102 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 435
Experimental & physicochemical properties
DrugsPharmaceuticals
Solubility<1 mg/mL
Melting Point179-180 ºC
Collision Cross Section171.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID0023743]
Physicochemical properties
- FDA UNII
- 1 B5910V2 · TN1B5910V2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - 1H-Purine-2,6-dione, 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxyethyl)methylamino]propyl]-1,3-dimethyl-: Environment tier I assessment
Chemistry & industry
Pharmacology
Protein BindingFrom the administered dose of xanthinol between 90.9 and 100% can be retreived in the plasma.
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.
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.
Biological Half-LifeThe reported elimination half-life of xanthinol is 1.67h.
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.
Absorption, Distribution and Excretion
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.
In urine, the two stereoisomeric forms of the xanthinol metabolites represents about 7-8% of the eliminated xanthinol.
The volume of distribution of xanthinol is 0.93 L/kg.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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