파라잔틴
파라잔틴 · PARAXANTHINE · Paraxanthin · Caffeine EP Impurity F · 1,7-dimethyl-3H-purine-2,6-dione · 1,7-Dimethyl-1H-purine-2,6-dione, 1,7-Dimethylxanthine, 2,6-Dihydroxy-1,7-dimethylpurine, Paraxanthine · 1,7-diMethyl-1H-purine-2,6(3H,7H)-dione · Paraxanthine-d3
식별자 및 물리적 특성
| CAS No. | 611-59-6 |
|---|---|
| 분자식 | C7H8N4O2 |
| 평균 분자량 | 180.16 g/mol |
| 단동위원소 질량 | 180.06472551 g/mol |
| SMILES | Cn1c(=O)[nH]c2ncn(C)c2c1=O |
| InChIKey | QUNWUDVFRNGTCO-UHFFFAOYSA-N |
| PubChem CID | 4687 |
| ChEMBL | CHEMBL1158 |
| ChEBI | CHEBI:25858 |
| EC No. | 210-271-9 |
| DTXSID | DTXSID2052281 |
| 현지명 | 파라잔틴 |
화학 및 물리적 성질
| XLogP | -0.2 |
|---|---|
| 극성 표면적 | 67.2 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 13 |
| 형식 전하 | 0 |
| 복잡도 | 267 |
| 용해도 | >27 [ug/mL] (The mean of the results at pH 7.4)에탄올: 0.6mg/mL |
| 녹는점 | 351 - 352 °C294-296 °C (lit.) |
| Physical Description | Faint yellow fine crystals[MSDSonline]Solid |
| Collision Cross Section | 134.2 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID2052281]136.8 Ų [M-H]- [CCS Type: DTIonization: ESI-149.5 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]134 Ų [M+H]+ [CCS Type: DT138.7 Ų [M+H]+ [CCS Type: DT130.85 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]137.69 Ų [M+K]+ [CCS Type: TW125.98 Ų [M+H-H2O]+ [CCS Type: TW138.86 Ų [M+Na]+ [CCS Type: TW132.4 Ų [M+H]+ [CCS Type: TW135.63 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]133.24 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| 끓는 점 | 312.97°C (rough estimate) |
| 밀도 | 1.3640 (rough estimate) |
| 굴절률 | 1.6700 (estimate) |
| 인화점 | 9℃ |
| 저장 조건 | room temp |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | pKa 8.5 (Uncertain) |
| 색상 | 하얀색 |
| BRN | 197907 |
| 안정성 | 실온에서 단단히 밀봉하여 보관하십시오. |
| 화장품 원료 기능 | 피부 컨디셔닝 |
| 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 | 1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl- (611-59-6) |
화학적 성질
Off-White to Pale Yellow Solid
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.WarningH302 (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. |
|---|---|
| 유해성 요약 | A skin, eye, and respiratory tract irritant[MSDSonline] |
| Hazard Classes and Categories | Acute Tox. 4 (93.3%) |
| USGS Health-Based Screening Levels for Evaluating Water-Quality | 1,7-DimethylxanthinePharmaceuticalSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | RV9380000 |
| 운송 번호(UN) | UN1230 - class 3 - PG 2 - Methanol, solution |
| 독성 | mmo-esc 150 mg/L CSHSAZ 16,337,52 |
| 관세 코드 | 2933.59.9500 |
| 위험 문구(R) | 22-39/23/24/25-23/24/25-11 |
| 위험 표시 | Xn,T,F |
| 안전 문구(S) | 22-24/25-45-36/37-16-7 |
| 위험 등급 | Acute Tox. 4 Oral |
| 저장 분류 |
용도
개요
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.
용도
1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).
일반 설명
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.