8-Cyclopentyl-1,3-dimethylxanthine - CAS 35873-49-5
Category: Inhibitor
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Molecular Formula:
C12H16N4O2
Molecular Weight:
248.28
COA:
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Targets:
Adenosine Receptor
Description:
8-Cyclopentyl-1,3-dimethylxanthine is a selective and high affinity adenosine A1 receptor antagonist. Its pKi value is 7.5-8.
Purity:
≥99% by HPLC
Synonyms:
8-Cyclopentyl-3,9-dihydro-1,3-dimethyl-1H-purine-2,6-dione; CPT; 8-Cyclopentyltheophylline
MSDS:
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InChIKey:
SCVHFRLUNIOSGI-UHFFFAOYSA-N
InChI:
InChI=1S/C12H16N4O2/c1-15-10-8(11(17)16(2)12(15)18)13-9(14-10)7-5-3-4-6-7/h7H,3-6H2,1-2H3,(H,13,14)
Canonical SMILES:
CN1C2=C(C(=O)N(C1=O)C)NC(=N2)C3CCCC3
1.8-Cyclopentyl 1,3-dimethylxanthine prolongs epileptic seizures in rats.
Dragunow M;Robertson HA Brain Res. 1987 Aug 11;417(2):377-9.
We tested the effects of 8-cyclopentyl-1,3 dimethylxanthine (8-CPT) on electrically induced seizures in rats. 8-CPT prolonged secondary seizures and converted partial seizures into generalized motor seizures, but did not affect primary seizure duration. Because 8-CPT is a potent and specific adenosine antagonist, these results add further support to the hypothesis that endogenous adenosine prevents the spread of epileptic seizures.
2.Adenosine receptor ligands and cocaine in conditioned place preference (CPP) test in rats.
Poleszak E;Malec D Pol J Pharmacol. 2002 Mar-Apr;54(2):119-26.
The influence of adenosine receptor agonists and antagonists on cocaine--induced conditioned place preference (CPP) was examined in male Wistar rats. Adenosine receptor agonists, when given alone, induced place preference in some dose ranges, and it seems that adenosine A1 and A2 receptors might be involved in this reaction. All adenosine receptor agonists: 2-p-(2-carboxyethyl)phenethylamino-5'-N-ethylcarboxamidoadenosine (CGS 21680), A2A receptor agonist, N6-cyclopentyladenosine (CPA), A1 receptor agonist, and 5'-N-ethylcarboxamidoadenosine (NECA), A2/A1 receptor agonist did not prevent the acquisition of cocaine-induced CPP but, when administered at the lower doses, they reduced the expression of cocaine action in CPP test. Selective adenosine A1 receptor antagonist, 8-cyclopentyltheophylline (CPT), A2 receptor antagonist, 3,7-dimethyl-1-propargylxanthine, DMPX, and caffeine (non-selective A1/A2 receptor antagonist) markedly and significantly decreased the expression of CPP induced by cocaine, and caffeine (20 mg/kg) decreased also the acquisition of this reaction. Our results suggest the involvement of adenosine A1 and A2 receptors in rewarding properties of cocaine measured in CPP test.
3.The effect of oxygen and adenosine on lizard thermoregulation.
Petersen AM;Gleeson TT;Scholnick DA Physiol Biochem Zool. 2003 May-Jun;76(3):339-47.
A regulated decrease in internal body temperature (Tb) appears to play a protective role against metabolic disruptions such as exposure to ambient hypoxia. This study examined the possibility that Tb depression is initiated when low internal oxygen levels trigger the release of adenosine, a neural modulator known to influence thermoregulation. We measured selected Tb of Anolis sagrei in a thermal gradient under varied ambient oxygen conditions and following the administration of the adenosine receptor antagonist 8-cyclopentyltheophylline (CPT). The average decrease in Tb observed following exposure to hypoxia (<10% O2) and following exhaustive exercise were 5 degrees and 3 degrees C, respectively, suggesting a role of oxygen availability on initiation of regulated hypothermia. When A. sagrei were run to exhaustion and recovered in hyperoxic (>95% O2) conditions, exercise-induced Tb depression was abolished. Administration of CPT similarly abolished decreased Tb due to both exercise and hypoxia. Trials using Dipsosaurus dorsalis indicate that elevated ambient oxygen during exercise does not influence blood pH or lactate accumulation, suggesting that these factors do not initiate changes in thermoregulatory setpoint following exhaustive exercise.
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