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Key Documents

COO/COA

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

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)

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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

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’.

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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)

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)

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)

Control of methylxanthines in the competition horse: pharmacokinetic/pharmacodynamic studies on caffeine, theobromine and theophylline for the assessment of irrelevant concentrations.

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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Articles

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.