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D5385

Sigma-Aldrich

1,7-Dimethylxanthine

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

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C7H8N4O2
Numero CAS:
611-59-6
Peso molecolare:
180.16
Beilstein:
197907
Numero CE:
210-271-9
Numero MDL:
MFCD00005727
Codice UNSPSC:
41106305
ID PubChem:
24277678
NACRES:
NA.77

product name

1,7-Dimethylxanthine, ~98%, solid

Saggio

~98%

Livello qualitativo

200

Forma fisica

solid

Colore

white

Punto di fusione

294-296 °C (lit.)

Solubilità

ethanol: 0.6 mg/mL
H2O: 1 mg/mL
0.1 M NaOH: 2 mg/mL

Stringa SMILE

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)
QUNWUDVFRNGTCO-UHFFFAOYSA-N

Informazioni sul gene

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

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Descrizione generale

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

Applicazioni

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

Azioni biochim/fisiol

Adenosine receptor ligand; major metabolite of caffeine

Caratteristiche e vantaggi

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302

Classi di pericolo

Acute Tox. 4 Oral

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Theophylline anhydrous, ≥99%, powder

Sigma-Aldrich

T1633

Theophylline

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

Sigma-Aldrich

725625

Caffeine-(trimethyl-d9)

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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Articoli

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.

Contenuto correlato

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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