N-[2-(4-Aminophenyl)ethyl]-adenosine - CAS 89705-21-5
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Adenosine Receptor
N6-[2-(4-Aminophenyl)ethyl]adenosine is a potent, non-selective adenosine A3 adenosine receptor agonist. It could enhance the protective activity of carbamazepine and the protective activity potentiates most likely through the A subtype of adenosine receptors at low doses. It also enhances the anticonvulsive effect of other antiepileptics via adenosine A1 receptors at higher doses. It has no significant effect on seizure parameters in amygdala-kindled rats in vivo. It is combined with antiepileptic drugs administered at doses ineffective in fully kindled rats.
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APNEA;Adenosine, N6-2-(4-aminophenyl)ethyl;(2R,3R,4S,5R)-2-[6-[2-(4-aminophenyl)ethylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
10 mM in DMSO
N6-[2-(4-Aminophenyl)ethyl]adenosine could enhance the protective activity of carbamazepine. It also enhances the anticonvulsive effect of other antiepileptic.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Boiling Point:
781.8±70.0 °C | Condition: Press: 760 Torr
1.65±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
Canonical SMILES:
1.Adenosine receptors mediate both contractile and relaxant effects of adenosine in main pulmonary artery of guinea pigs.
Szentmiklósi AJ1, Ujfalusi A, Cseppentö A, Nosztray K, Kovács P, Szabó JZ. Naunyn Schmiedebergs Arch Pharmacol. 1995 Apr;351(4):417-25.
In guinea pig main pulmonary artery precontracted with noradrenaline, adenosine exerted an initial phasic contraction followed by a tonic contraction and a slow relaxation. After selective blockade by 1,3-dipropyl-8-cyclopentylxanthine (DPCPX: 10 nM) of A1 receptors, adenosine only elicited a rapid relaxation. This initial response was characterized by use of adenosine (AR) and its analogues N6-cyclopentyl-adenosine (CPA), R-N6-phenylisopropyladenosine (R-PIA), 2-chloroadenosine (CADO), 5'-N-ethyl-carboxamidoadenosine(NECA), N6-2-(4-aminophenyl) ethyl adenosine (APNEA) and 2-p-((carboxyethyl)-phenethylamino)-5'-carboxamidoadenosine (CGS 21 680). The order of potency of the adenosine analogues for purine-induced phasic contraction was CPA > R-PIA > NECA = APNEA > AR > CGS 21 680 suggesting the involvement of activation of A1 type adenosine receptors in the contraction phase. DPCPX antagonized the CPA-induced contraction with a pA2 = 9.
2.The role of intraspinal adenosine A1 receptors in sympathetic regulation.
Peng SC1, Ho CM, Ho ST, Tsai SK, Su CK. Eur J Pharmacol. 2004 May 10;492(1):49-55.
Using a splanchnic nerve-spinal cord preparation in vitro, we have previously demonstrated that tonic sympathetic activity is generated from the thoracic spinal cord. Here, we sought to determine if adenosine receptors play a role in modulating this spinally generated sympathetic activity. Various adenosine analogs were applied. N6-Cyclopentyladenosine (CPA, adenosine A1 receptor agonist) and 5'-N-ethylcarboxamidoadenosine (NECA, adenosine A1/A2 receptor agonist) reduced, while N6-[2-(4-aminophenyl)ethyl]adenosine (APNEA, non-selective adenosine A3 receptor agonist) did not alter sympathetic activity. The inhibitory effect of CPA or NECA on sympathetic activity was reversed by 8-cyclopentyltheophylline (CPT, adenosine A1 receptor antagonist) or abolished by CPT pretreatment. In the presence of 3,7-dimethyl-1-propargylxanthine (DMPX, adenosine A2 receptor antagonist), sympathetic activity was still reduced by CPA or NECA. Sympathetic activities were not changed by applications of the more selective adenosine A2 or A3 receptor agonists or antagonists, including 4-[2-[[6-amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid (CGS21680), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-a][1,3,5]triazin-5-ylamino]ethyl)phenol (ZM241385), 2-chloro-N6-(3-iodobenzyl)-adenosine-5'-N-methyluronamide (Chloro-IB-MECA), and 3-ethyl-5-benzyl-2-methyl-4-phenylethynyl-6-phenyl-1,4-(+/-)-dihydropyridine-3,5-dicarboxylate (MRS1191).
3.Functional characterization of adenosine receptors in the nucleus tractus solitarius mediating hypotensive responses in the rat.
White PJ1, Rose'Meyer RB, Hope W. Br J Pharmacol. 1996 Jan;117(2):305-8.
1. The aim of this study was to characterize adenosine receptors located in the nucleus tractus solitarius (NTS) that mediate decreases in blood pressure in the anaesthetized rat. To determine the adenosine receptor subtype involved, a range of selective agonists and antagonists were studied and their relative potencies evaluated. 2. The rank order of agonist potency in inducing decreases in diastolic blood pressure was N6-cyclopentyladenosine (CPA) > N6-cyclohexyladenosine (CHA) > N-ethyl-carboxamidoadenosine (NECA) > or = 2-phenylaminoadenosine (CV1808) > 2-p-(carboxyethyl)phenethylamino-5' N-ethylcarboxamidoadenosine (CGS 21680) > N6-(2-(4-aminophenyl)ethyl)-adenosine (APNEA). 3. The hypotensive action of CPA following microinjection into the NTS was antagonized by i.v. infusions (50 micrograms kg-1 min-1) of adenosine receptor antagonists, 8-cyclopentyl-1,3 dipropylxanthine (DPCPX), 8-phenyltheophylline (8-PT), 8-(p-sulphophenyl)theophylline (8-SPT), and 1,3-dipropyl-8-N-(2-diethylamino)ethyl)-N methyl-4-(2,3,6,7-tetrahydro-2,6-dioxo) benzenesulphonamidexanthine (PD 115199).
4.Demonstration of both A1 and A2 adenosine receptors in DDT1 MF-2 smooth muscle cells.
Ramkumar V1, Barrington WW, Jacobson KA, Stiles GL. Mol Pharmacol. 1990 Feb;37(2):149-56.
Adenosine receptors of the A1 and A2 subtypes were characterized in membranes from DDT1 MF-2 smooth muscle cells. These cells possess a high density of A1 adenosine receptors (Bmax = 0.8-0.9 pmol/mg of protein), as measured by both agonist and antagonist radioligands. Agonists compete for [125I]N6-[2-(4-amino-3-iodophenyl)ethyl]-adenosine (A1 receptor-selective radioligand) binding with the following potency series: (R)-phenylisopropyladenosine [(R)-PIA] greater than 5'-N-ethylcarboxamide adenosine (NECA) greater than (S)-PIA, indicative of their interaction with A1 adenosine receptors. Agonist competition for [3H]8-(4-[[[(2-aminoethyl)amino]carbonyl)methyl)oxy]phenyl)-1, 3-dipropylxanthine [( 3H]XAC) (an antagonist radioligand for the A1 adenosine receptor) was described by a two-state model of 1.3 nM (high affinity state, KK) and 370 nM (low affinity state, KL), with 70% of the receptors in the high affinity state (RH). Addition of guanosine 5'-[beta, alpha-imido]triphosphate (100 microM) shifted the (R)-PIA competition curves to the right to lower affinities.
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CAS 89705-21-5 N-[2-(4-Aminophenyl)ethyl]-adenosine

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