D5385
1,7-二甲基黄嘌呤
~98% (TLC), solid, adenosine receptor ligand
别名:
1,7-二甲基-1H-嘌呤-2,6-二酮, 1,7-二甲基-3,7-二氢-1H-嘌呤-2,6-二酮, 2,6-二氢-1,7-二甲基嘌呤, NSC 400018, Paraxanthine
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关于此项目
经验公式（希尔记法）:
C7H8N4O2
化学文摘社编号:
分子量:
180.16
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
210-271-9
MDL number:
Beilstein/REAXYS Number:
197907
产品名称
1,7-二甲基黄嘌呤, ~98%, solid
Quality Level
InChI key
QUNWUDVFRNGTCO-UHFFFAOYSA-N
InChI
1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
SMILES string
CN1C(=O)Nc2ncn(C)c2C1=O
assay
~98%
form
solid
color
white
mp
294-296 °C (lit.)
solubility
ethanol: 0.6 mg/mL
H2O: 1 mg/mL
0.1 M NaOH: 2 mg/mL
Gene Information
human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369)
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Application
1,7-二甲基黄嘌呤已用于咖啡因的高效液相色谱(HPLC)定量。
Biochem/physiol Actions
腺苷受体配体；咖啡因的主要代谢物
Features and Benefits
这种化合物是环核苷酸研究的特色产品。点击此处发现更多特色环核苷酸产品。在sigma.com/discover-bsm可了解更多关于生物活性小分子的其他研究领域。
General description
1,7-二甲基黄嘌呤是咖啡因的初级代谢产物。具有增进机能和拟交感作用。
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
存储类别
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Paraxanthine, a caffeine metabolite, dose dependently increases [Ca2+] i in skeletal muscle
Hawke TJ, et al.
Journal of Applied Physiology, 89(6), 2312-2317 (2000)
S Ferré et al.
European journal of pharmacology, 179(3), 295-299 (1990-04-25)
We present evidence showing that paraxanthine (1,7-dimethylxanthine), the main metabolite of caffeine in man, displaces the binding of [3H]SCH 23390, a radioligand which selectively labels dopamine D-1 receptors when used at low concentrations, from striatal membranes of the rat. The
Paraxanthine, the primary metabolite of caffeine, provides protection against dopaminergic cell death via stimulation of ryanodine receptor channels
Guerreiro S, et al.
Molecular Pharmacology, 74(4), 980-989 (2008)
HPLC method for quantification of caffeine and its three major metabolites in human plasma using fetal bovine serum matrix to evaluate prenatal drug exposure
Lopez-Sanchez RDC, et al.
Journal of Analytical Methods in Chemistry, 2018 (2018)
Rozalia-Maria Anastasiadi et al.
Antioxidants (Basel, Switzerland), 10(1) (2020-12-31)
The enzyme CYP1A2 is responsible for the metabolism of numerous antioxidants in the body, including caffeine, which is transformed into paraxanthine, its main primary metabolite. Both molecules are known for their antioxidant and pro-oxidant characteristics, and the paraxanthine-to-caffeine molar ratio
商品
Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.
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