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Merck
CN

P2278

1,3-Dimethyl-8-phenylxanthine

crystalline

Synonym(s):

8-Phenyltheophylline

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About This Item

Empirical Formula (Hill Notation):
C13H12N4O2
CAS Number:
961-45-5
Molecular Weight:
256.26
UNSPSC Code:
12352200
NACRES:
NA.77
PubChem Substance ID:
24278626
MDL number:
MFCD00005582
Beilstein/REAXYS Number:
261704

Key Documents

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solubility

aqueous base: moderately soluble (Solutions should be stored at 4 °C.), ethanol: moderately soluble (Solutions should be stored at 4 °C.), H2O: slightly soluble

InChI

1S/C13H12N4O2/c1-16-11-9(12(18)17(2)13(16)19)14-10(15-11)8-6-4-3-5-7-8/h3-7H,1-2H3,(H,14,15)

SMILES string

CN1C(=O)N(C)c2nc([nH]c2C1=O)-c3ccccc3

InChI key

PJFMAVHETLRJHJ-UHFFFAOYSA-N

form

crystalline

potency

86 nM Ki for A1 receptors

color

off-white to light yellow

mp

>300 °C (lit.)

Gene Information

human ... ADORA1(134), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora2b(29316)

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Biochem/physiol Actions

Selective A1 adenosine receptor antagonist.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBF6156V
MKBF6156
06613HH
017K3701
123K3738

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W R Ezzat et al.
The American journal of physiology, 252(4 Pt 2), H836-H845 (1987-04-01)
Pressure-flow autoregulation, although weak, was seen in the hepatic artery (HA) of every cat that also showed dilation to infused adenosine. Several means of quantitating autoregulation are described and evaluated, and all indices showed that the selective adenosine antagonists, 8-phenyltheophylline
J Sawynok et al.
Neuropharmacology, 30(8), 871-877 (1991-08-01)
Morphine was injected into the periaqueductal gray region of the rat and 8-phenyltheophylline, an adenosine receptor antagonist, was injected intrathecally 15 or 30 min later, to determine whether supraspinally-administered morphine activated descending mechanisms to release adenosine (or a nucleotide which
Daphne Merkus et al.
American journal of physiology. Heart and circulatory physiology, 285(1), H424-H433 (2003-03-15)
In dogs, only combined blockade of vasodilator pathways [via adenosine receptors, nitric oxide synthase (NOS) and ATP-sensitive K+ (KATP) channels] results in impairment of metabolic vasodilation, which suggests a redundancy design of coronary flow regulation. Conversely, in swine and humans
Ana Rita Pinheiro et al.
Cell communication and signaling : CCS, 11, 70-70 (2013-09-21)
Chronic musculoskeletal pain involves connective tissue remodeling triggered by inflammatory mediators, such as bradykinin. Fibroblast cells signaling involve changes in intracellular Ca2+ ([Ca2+]i). ATP has been related to connective tissue mechanotransduction, remodeling and chronic inflammatory pain, via P2 purinoceptors activation.
Gregory M Dick et al.
American journal of physiology. Heart and circulatory physiology, 294(5), H2371-H2381 (2008-04-01)
We previously demonstrated a role for voltage-dependent K(+) (K(V)) channels in coronary vasodilation elicited by myocardial metabolism and exogenous H(2)O(2), as responses were attenuated by the K(V) channel blocker 4-aminopyridine (4-AP). Here we tested the hypothesis that K(V) channels participate
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