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D5385

Sigma-Aldrich

1,7-Dimethylxanthine

~98% (TLC), solid, adenosine receptor ligand

Sinónimos:

1,7-Dimethyl-1H-purine-2,6-dione, 1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione, 2,6-Dihydroxy-1,7-dimethylpurine, NSC 400018, Paraxanthine

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About This Item

Fórmula empírica (notación de Hill):
C7H8N4O2
Número de CAS:
611-59-6
Peso molecular:
180.16
Beilstein/REAXYS Number:
197907
EC Number:
210-271-9
MDL number:
MFCD00005727
UNSPSC Code:
41106305
PubChem Substance ID:
24277678
NACRES:
NA.77

Nombre del producto

1,7-Dimethylxanthine, ~98%, solid

assay

~98%

Quality Level

200

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

SMILES string

CN1C(=O)Nc2ncn(C)c2C1=O

InChI

1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)

InChI key

QUNWUDVFRNGTCO-UHFFFAOYSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369)

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General description

1,7-Dimethylxanthine is a primary metabolite of caffeine. It has ergogenic and sympathomimetic effects.

Application

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

Biochem/physiol Actions

Adenosine receptor ligand; major metabolite of caffeine

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
069M4150V
118K1448V
13181156
067M4162V
13170112

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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
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)
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)
Marc Machnik et al.
Drug testing and analysis, 9(9), 1372-1384 (2016-09-24)
Methylxanthines positives in competition samples have challenged doping control laboratories and racing jurisdictions since methylxanthines are naturally occurring prohibited substances and often constituents of feed. For theobromine, an international threshold (renamed in International Residue Limit, IRL) of 2 µg/mL in urine
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HPLC Analysis of Xanthines on Purospher® STAR RP-18 endcapped

Xanthine is a purine base found in most human body tissues and fluids as well as in other organisms. Methylated xanthines (methylxanthines), which include caffeine, paraxanthine, theobromine, and theophylline, commonly used for their effects as mild stiµlants and as bronchodilators, notably in the treatment of asthma symptoms. This application shows the efficient separation of several common xanthines and may be applied their analysis in any number of desired matrices.

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Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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