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3,7-ジヒドロ-7-[2-ヒドロキシ-3-[(2-ヒドロキシエチル)メチルアミノ]プロピル]-1,3-ジメチル-1H-プリン-2,6-ジオン

Xanthinol

HCID 9913
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
2530-97-4
標準SMILES
CN(CCO)CC(O)Cn1cnc2c1c(=O)n(C)c(=O)n2C
InChIKey
DSFGXPJYDCSWTA-UHFFFAOYSA-N
分子式
C13H21N5O4
平均分子量
311.34 g/mol
単同位体質量
311.15935417

概要

7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione is an oxopurine.

名称と識別子

優先名称
Xanthinol
IUPAC
7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione
現地名
3,7-ジヒドロ-7-[2-ヒドロキシ-3-[(2-ヒドロキシエチル)メチルアミノ]プロピル]-1,3-ジメチル-1H-プリン-2,6-ジオン
英語名
Xanthinol
分子式
C13H21N5O4
分子量
311.34

名称と別名

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
名称をさらに表示
7-[2-ヒドロキシ-3-[N-(2-ヒドロキシエチル)-N-メチルアミノ]プロピル]-1,3-ジメチル-1H-プリン-2,6(3H,7H)-ジオン1,3-ジメチル-3,7-ジヒドロ-7-[2-ヒドロキシ-3-[(2-ヒドロキシエチル)メチルアミノ]プロピル]-1H-プリン-2,6-ジオン7-[2-ヒドロキシ-3-[N-(2-ヒドロキシエチル)-N-メチルアミノ]プロピル]テオフィリンキサンチノール3,7-ジヒドロ-7-[2-ヒドロキシ-3-[(2-ヒドロキシエチル)メチルアミノ]プロピル]-1,3-ジメチル-1H-プリン-2,6-ジオン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-dione

物性

構造計算による物性

XLogP
-1.8
極性表面積
102 Ų
水素結合供与体数
2
水素結合受容体数
6
回転可能結合数
6
重原子数
22
形式電荷
0
複雑度
435

実験および物理化学的性質

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]

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

危険有害性情報

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

化学と産業

薬理情報

Protein BindingFrom the administered dose of xanthinol between 90.9 and 100% can be retreived in the plasma.
Pharmacodynamics · 1 件

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 · 1 件

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 · 1 件

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 · 4 件

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.

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
1H-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

データベース識別子

CAS
2530-97-4
PubChem CID
9913
DTXSID
DTXSID1048255
ChEMBL
CHEMBL1624126
ChEBI
CHEBI:94314
UNII
TN1B5910V2
Nikkaji
J7.603A

The total body clearance rate for xanthinol is 0.63 L h/kg.

上流・下流製品情報

上流原料

1H-Purine-2,6-dione, 7-(3-chloro-2-hydroxypropyl)-3,7-dihydro-1,3-dimethyl-, (+)-1,3-ジメチル-7-(オキシラニルメチル)-1,2,3,6-テトラヒドロ-7H-プリン-2,6-ジオン2-(メチルアミノ)エタノール

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