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Key Documents

P2278

Sigma-Aldrich

1,3-Dimethyl-8-phenylxanthine

crystalline

Synonym(s):

8-Phenyltheophylline

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About This Item

Empirical Formula (Hill Notation):
C13H12N4O2
CAS Number:
Molecular Weight:
256.26
Beilstein:
261704
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

form

crystalline

potency

86 nM Ki for A1 receptors

color

off-white to light yellow

mp

>300 °C (lit.)

solubility

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

SMILES string

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

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)

InChI key

PJFMAVHETLRJHJ-UHFFFAOYSA-N

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Biochem/physiol Actions

Selective A1 adenosine receptor antagonist.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
Simin Khavandgar et al.
Neurobiology of learning and memory, 78(2), 390-405 (2002-11-15)
Pretraining administration of morphine (5 mg/kg, intraperitonically) in a step-down passive avoidance task led to state-dependent learning with impaired retrieval on the test day that was dose-dependently restored by pretest administration of morphine (0.5, 1, 3, and 5 mg/kg). This
John M Haynes et al.
Clinical and experimental pharmacology & physiology, 30(5-6), 329-335 (2003-07-16)
1. The effects of ATP, the stable ATP analogues alpha,beta-methylene ATP (alpha,beta-mATP), 2-methylthioATP (2meSATP) and adenosine tetraphosphate (ATP4), the pyrimidine nucleotide uridine 5'-triphosphate (UTP) and the alpha1-adrenoceptor agonist phenylephrine were examined on the isolated perfused uterine vasculature of dioestrous, oestradiol-treated
J E Coelho et al.
Neuroscience, 138(4), 1195-1203 (2006-01-31)
Activation of A1 adenosine receptors is important for both the neuromodulatory and neuroprotective effects of adenosine. However, short periods of global ischemia decrease A1 adenosine receptor density in the brain and it is not known if a parallel loss of

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