Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

D5385

Sigma-Aldrich

1,7-Dimethylxanthine

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

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C7H8N4O2
CAS Number:
611-59-6
Molecular Weight:
180.16
Beilstein:
197907
EC Number:
210-271-9
MDL number:
MFCD00005727
UNSPSC Code:
41106305
PubChem Substance ID:
24277678
NACRES:
NA.77

product name

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)

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Theophylline anhydrous, ≥99%, powder

Sigma-Aldrich

T1633

Theophylline

Caffeine-(trimethyl-d9) 99 atom % D, 98% (CP)

Sigma-Aldrich

725625

Caffeine-(trimethyl-d9)

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)
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, a caffeine metabolite, dose dependently increases [Ca2+] i in skeletal muscle
Hawke TJ, et al.
Journal of Applied Physiology, 89(6), 2312-2317 (2000)
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
View All Related Papers

Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service