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D134

Sigma-Aldrich

3,7-Dimethyl-1-propargylxanthine

≥98% (HPLC), powder

Synonyme(s) :

3,7-Dimethyl-1-(2-propynyl)xanthine, DMPX

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About This Item

Formule empirique (notation de Hill):
C10H10N4O2
Numéro CAS:
14114-46-6
Poids moléculaire :
218.21
Numéro MDL:
MFCD00078576
Code UNSPSC :
12352200
ID de substance PubChem :
24277754
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 15 mg/mL, clear

Chaîne SMILES 

CN1C(=O)N(CC#C)C(=O)c2c1ncn2C

InChI

1S/C10H10N4O2/c1-4-5-14-9(15)7-8(11-6-12(7)2)13(3)10(14)16/h1,6H,5H2,2-3H3

Clé InChI

IORPOFJLSIHJOG-UHFFFAOYSA-N

Informations sur le gène

human ... ADORA2A(135) , ADORA2B(136)
rat ... Adora1(29290) , Adora2a(25369)

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Application

3,7-Dimethyl-1-propargylxanthine (DMPX) has been used as an A2 -adenosine receptor (AR) antagonist:
  • to study its effects on potential modulation of motor output elicited by epidural spinal stimulation (ESS)
  • to study the role of A2a receptor in elevating cyclic adenosine monophosphate (cAMP) levels
  • to study its effects on the cell viability of human gastric cancer cell line

Actions biochimiques/physiologiques

3,7-Dimethyl-1-propargylxanthine (DMPX) is a caffeine analog and A2-selective adenosine receptor (AR) antagonist.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Ming Yang et al.
Naunyn-Schmiedeberg's archives of pharmacology, 375(2), 133-144 (2007-02-21)
Antagonists of adenosine A2A receptors (A2A -antagonists) with different chemical structures have been developed by several pharmaceutical companies for the potential treatment of Parkinson's disease. Pharmacological characterization of these antagonists was incomplete, and different assay conditions were used in different
C E Müller et al.
Journal of medicinal chemistry, 40(26), 4396-4405 (1998-01-22)
A series of 8-substituted derivatives of 3,7-dimethyl-1-propargylxanthine (DMPX) was synthesized and investigated as A2A adenosine receptor antagonists. Different synthetic strategies for the preparation of DMPX derivatives and analogues were explored. A recently developed synthetic procedure starting from 3-propargyl-5,6-diaminouracil proved to
Gabriele Pizzino et al.
Frontiers in pharmacology, 8, 558-558 (2017-09-21)
Glucocorticoid-induced osteoporosis (GIO) is a secondary cause of bone loss. Bisphosphonates approved for GIO, might induce jaw osteonecrosis; thus additional therapeutics are required. Adenosine receptor agonists are positive regulators of bone remodeling, thus the efficacy of adenosine receptor stimulation for
Maria Grazia Zizzo et al.
British journal of pharmacology, 148(7), 956-963 (2006-07-19)
The aims of the present study were firstly, to characterize pharmacologically the subtypes of P(1) purinoreceptors involved in the inhibitory effects induced by exogenous adenosine in longitudinal smooth muscle of mouse colon, and secondly, to examine differences in the function
Hanjeong Harvey et al.
Journal of bacteriology, 191(21), 6513-6524 (2009-09-01)
PilA, the major pilin subunit of Pseudomonas aeruginosa type IV pili (T4P), is a principal structural component. PilA has a conserved C-terminal disulfide-bonded loop (DSL) that has been implicated as the pilus adhesinotope. Structural studies have suggested that DSL is
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