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D134

Sigma-Aldrich

3,7-Dimethyl-1-propargylxanthine

≥98% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H10N4O2
CAS Number:
14114-46-6
Molecular Weight:
218.21
MDL number:
MFCD00078576
UNSPSC Code:
12352200
PubChem Substance ID:
24277754
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

SMILES string

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

InChI key

IORPOFJLSIHJOG-UHFFFAOYSA-N

Gene Information

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

Biochem/physiol Actions

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Hanjeong Harvey et al.
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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
Annika Thorsell et al.
Alcoholism, clinical and experimental research, 31(8), 1302-1307 (2007-06-07)
It has been suggested that the reinforcing properties of ethanol are in part mediated via an A2 activation of cAMP/PKA signaling in the nucleus accumbens, predicting that administration of an A2a antagonist might reduce ethanol reward and consumption. We therefore
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
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
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