Paraxanthine (HCID 4687)

名称と識別子

優先名称: Paraxanthine
IUPAC: 1,7-dimethyl-3H-purine-2,6-dione
現地名: パラキサンチン
英語名: 1,7-Dimethylxanthine
分子式: C7H8N4O2
分子量: 180.16

名称と別名

paraxanthine1,7-Dimethylxanthine611-59-6p-Xanthine1,7-dimethyl-3H-purine-2,6-dione1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl-DTXSID20522811,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dioneNSC-400018Q3565Y41V7DTXCID2030853

名称をさらに表示

1,7-ジメチル-7H-プリン-2,6(1H,3H)-ジオン1,7-ジメチル-2-ヒドロキシ-1,7-ジヒドロ-6H-プリン-6-オン1,7-ジメチルキサンチン1,7-ジメチル-2,3,6,7-テトラヒドロ-1H-プリン-2,6-ジオン3,7-ジヒドロ-1,7-ジメチル-1H-プリン-2,6-ジオンパラキサンチン2-ヒドロキシ-1,7-ジメチル-6,7-ジヒドロ-1H-プリン-6-オンParaxanthin1,7-Dimethyl-1H-purine-2,6-dione, 1,7-Dimethylxanthine, 2,6-Dihydroxy-1,7-dimethylpurine, ParaxanthineParaxanthine-d3Paraxanthine solution

CHEBI:25858RefChem:417792210-271-91,7-Dimethyl-1H-purine-2,6(3H,7H)-dione3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneXanthine, 1,7-dimethyl-Caffeine Impurity FCaffeine EP Impurity F

データベース識別子

CAS: 611-59-6
PubChem CID: 4687
DTXSID: DTXSID2052281
ChEMBL: CHEMBL1158
ChEBI: CHEBI:25858
UNII: Q3565Y41V7
EC Number: 210-271-9
Nikkaji: J2.991B

物性

構造計算による物性

XLogP: -0.2
極性表面積: 67.2 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 0
重原子数: 13
形式電荷: 0
複雑度: 267

実験および物理化学的性質

Solubility>27 [ug/mL] (The mean of the results at pH 7.4)

Melting Point351 - 352 °C

Physical Description · 2 件

Faint yellow fine crystals; [MSDSonline]

Solid

Collision Cross Section · 6 件

134.2 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2052281]；136.8 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID2052281]

149.5 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；134 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；138.7 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

130.85 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；137.69 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；125.98 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；138.86 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

132.4 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

135.63 Å² [M+H]+ [CCS Type: DT; Method: stepped-field]

133.24 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

物理化学的性質

融点: 294 · 294-296 °C (lit.)
沸点: 312.97 °C · 312.97°C (rough estimate)
比重(密度): 1.364 · 1.3640 (rough estimate)
屈折率: 1.67 · 1.6700 (estimate)
闪点: 9 ℃ · 9℃
貯蔵温度: room temp
溶解性: 0.6 mg/mL · エタノール：0.6mg/mL
外見: 個体
酸解離定数(Pka): 8.5 · pKa 8.5 (Uncertain)
色: 白い
BRN: 197907 · 197907
安定性: 室温で密閉して保管
化粧品成分の機能: スキンコンディショニング
InChI: InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChIKey: QUNWUDVFRNGTCO-UHFFFAOYSA-N
SMILES: N1(C)C2=C(NC(=O)N(C)C2=O)N=C1
EPAの化学物質情報: 1 H-Purine-2,6-dione, · 1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl- (611-59-6)

化学的性質

化学的特性Off-White to Pale Yellow Solid

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.

Warning

H302 (93.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 3 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 3 of 45 reports by companies.；There are 2 notifications provided by 42 of 45 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Hazards SummaryA skin, eye, and respiratory tract irritant; [MSDSonline]

Hazard Classes and CategoriesAcute Tox. 4 (93.3%)

毒性情報

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 件

1,7-Dimethylxanthine

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

安全データ

wgk: 3
rtecs: RV9380000
ridadr: UN1230 - class 3 - PG 2 - Methanol, solution
毒性: mmo-esc 150 mg/L CSHSAZ 16,337,52
hs_code: 2933.59.9500
risk_code: 22-39/23/24/25-23/24/25-11
hazard_code: Xn,T,F
safety_code: 22-24/25-45-36/37-16-7
Hazard Classifications: Acute Tox. 4 Oral
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Metabolism/MetabolitesParaxanthine has known human metabolites that include 1,7-Dimethyluric acid and 1-Methylxanthine.；Paraxanthine is a known human metabolite of caffeine.

Tissue LocationsKidney；Liver；Placenta；Prostate

Cellular LocationsCytoplasm

Metabolite PathwaysCaffeine Metabolism

用途と製造

Use ClassificationPharmaceuticals

応用分野 · 4 件

解説パラキサンチン，針状晶．融点298～299 ℃．pKa1 8.6．エタノール，エーテルに不溶，熱水，アンモニア水，塩酸に可溶．メチル化するとカフェインとなる．森北出版「化学辞典（第2版）

説明Paraxanthine is an inhibitor of phosphodiesterase 9 (PDE9) and an antagonist of adenosine receptors A1 and A2 (Kis = 35 and 22 μM, respectively in equine forebrain tissues). It is the main metabolite of caffeine in humans, making up 80% of the three dimethylxanthine metabolites produced by caffeine demethylation. Paraxanthine increases locomotor activity and counteracts adenosine receptor agonist-induced motor depression in rats not habituated to caffeine. At a dose of 30 mg/kg, paraxanthine induces a significant increase in striatal cGMP and extracellular striatal dopamine concentrations in vivo. It also promotes wakefulness and increases locomotor activity and core temperature in narcoleptic transgenic mice without increasing behavioral anxiety.

使用1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).

一般的な説明Paraxanthine is a major plasma and urinary metabolite of caffeine. This xanthine derivative is, along with caffeine, a central nervous system stimulant. This Snap-N-Spike reference solution is applicable for caffeine quantitation in clinical toxicology or urine drug testing by LC-MS/MS or GC/MS.

上流・下流製品情報

下流製品

テオフィリン

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

山东科立康药业有限公司053-88113608 17854192669

艾吉析科技（上海）有限公司17717235263 · [email protected]

補足説明

定義本品は、次の化学式で表される複素環式化合物である。

パラキサンチン

基本情報