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D5385

Sigma-Aldrich

1,7-Dimethylxanthine

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

Sinônimo(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

Fórmula empírica (Notação de Hill):
C7H8N4O2
Número CAS:
611-59-6
Peso molecular:
180.16
Beilstein:
197907
Número CE:
210-271-9
Número MDL:
MFCD00005727
Código UNSPSC:
41106305
ID de substância PubChem:
24277678
NACRES:
NA.77

Nome do produto

1,7-Dimethylxanthine, ~98%, solid

Ensaio

~98%

Nível de qualidade

200

Formulário

solid

cor

white

pf

294-296 °C (lit.)

solubilidade

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

cadeia de caracteres SMILES

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)

chave InChI

QUNWUDVFRNGTCO-UHFFFAOYSA-N

Informações sobre genes

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

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Descrição geral

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

Aplicação

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

Ações bioquímicas/fisiológicas

Adenosine receptor ligand; major metabolite of caffeine

Características e benefícios

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Declarações de precaução

P264 - P270 - P301 + P312 - P501

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

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

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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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Artigos

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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