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D5385

1,7-Dimethylxanthine

Name: 1,7-Dimethylxanthine
Brand: SIGMA

~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

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About This Item

Empirical Formula (Hill Notation):

C₇H₈N₄O₂

CAS Number:

611-59-6

Molecular Weight:

180.16

NACRES:

NA.77

PubChem Substance ID:

24277678

UNSPSC Code:

41106305

EC Number:

210-271-9

MDL number:

MFCD00005727

Beilstein/REAXYS Number:

197907

Assay:

~98%

Form:

solid

Quality level:

200

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Properties

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)

Description

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

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Articles

Discover Bioactive Molecules for Nucleotides

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

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)

Paraxanthine displaces the binding of [3H]SCH 23390 from rat striatal membranes.

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)

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Global Trade Item Number

SKU	GTIN
D5385-500MG	04061832897844
D5385-100MG	04061833586181