T4146
1,3,9-Trimethylxanthine
≥98% (HPLC), solid
Synonym(s):
2,6-Dihydroxy-1,3,9-trimethylpurine, Isocaffeine
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About This Item
Empirical Formula (Hill Notation):
C8H10N4O2
CAS Number:
Molecular Weight:
194.19
Beilstein/REAXYS Number:
196140
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
biological source
synthetic (organic)
assay
≥98% (HPLC)
form
solid
solubility
H2O: >20 mg/mL
storage temp.
room temp
SMILES string
CN1C(=O)N(C)c2c(ncn2C)C1=O
InChI
1S/C8H10N4O2/c1-10-4-9-5-6(10)11(2)8(14)12(3)7(5)13/h4H,1-3H3
InChI key
LPHGQDQBBGAPDZ-UHFFFAOYSA-N
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Application
1,3,9-Trimethylxanthine (Isocaffeine) may be used to study the mechanism of inositol-trisphosphate (Ins-P3) induced calcium release. 1,3,9-Trimethylxanthine may be used as an internal standard for measuring metabolites of caffeine in urine and other fluids by HPLC or capillary electrophoresis. 1,3,9-Trimethylxanthine may be used in studies on the binding of caffeine analogues to adenosine receptors.
Biochem/physiol Actions
1,3,9-Trimethylxanthine is an adenosine receptor antagonist.
Storage Class
13 - Non Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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L Missiaen et al.
The Biochemical journal, 300 ( Pt 1), 81-84 (1994-05-15)
We have investigated the effect of various methylxanthines on the basal and InsP3-stimulated unidirectional 45Ca2+ efflux from permeabilized A7r5 cells under different experimental conditions. We report that caffeine and theophylline inhibit the InsP3-induced Ca2+ release, whereas the basal Ca2+ leak
Yuli Liu et al.
The journal of physical chemistry. B, 115(47), 13880-13890 (2011-10-06)
Using the recently solved crystal structure of the human adenosine A(2A) receptor, we applied MM/PBSA to compare the binding modes of caffeine with those of the high-affinity selective antagonist ZM241385. MD simulations were performed in the environment of the lipid
N Rodopoulos et al.
Scandinavian journal of clinical and laboratory investigation, 54(4), 305-315 (1994-07-01)
Caffeine (CA) and its 14 main metabolites were determined in urine by reversed-phase high-performance liquid chromatography (RP-HPLC) and capillary electrophoresis (CE). After addition of 1,3,9-trimethylxanthine, uracil and beta-hydroxyethyltheophylline as internal standards, samples were separated by RP-HPLC into three fractions; A
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