8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H24N4O2
Molecular Weight	304.3874
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE

Structure Search

SMILES

CCCN1C2=C(N=C(N2)C3CCCC3)C(=O)N(CCC)C1=O

InChI

InChIKey=FFBDFADSZUINTG-UHFFFAOYSA-N

InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)

HIDE SMILES / InChI

Molecular Formula	C16H24N4O2
Molecular Weight	304.3874
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2825043 | https://www.ncbi.nlm.nih.gov/pubmed/7926579

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a selective high-affinity antagonist radioligand for A1 adenosine receptors. DPCPX is a useful tool with which to explore the potential of activation of adenosine A1 receptors as an important mechanism in physiological and pathophysiological processes.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A1 receptor 54 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2825043 \| https://www.ncbi.nlm.nih.gov/pubmed/3561384	Antagonist 2849		0.56 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Alcohol abuse 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26033424	Primary	Preclinical	Unknown Approved Use Unknown
Memory disorders 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25939452 https://www.ncbi.nlm.nih.gov/pubmed/25490060	Primary	Preclinical	Unknown Approved Use Unknown
Arrhythmia 45 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20334814 https://www.ncbi.nlm.nih.gov/pubmed/21907719 https://www.ncbi.nlm.nih.gov/pubmed/20962006	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacology of airway afferent nerve activity.	2001	11686889
The sulphydryl reagent, N-ethylmaleimide, disrupts sleep and blocks A1 adenosine receptor-mediated inhibition of intracellular calcium signaling in the in vitro ventromedial preoptic nucleus.	2001	11682159
Adenosine preferentially suppresses serotonin2A receptor-enhanced excitatory postsynaptic currents in layer V neurons of the rat medial prefrontal cortex.	2001	11483300
Subchronic treatment with methamphetamine and phencyclidine differentially alters the adenosine A1 and A2A receptors in the prefrontal cortex, hippocampus, and striatum of the rat.	2001 Apr	11495346
2-chloro-N(6)-cyclopentyladenosine-elicited attenuation of evoked glutamate release is not sufficient to give complete protection against pilocarpine-induced seizures in rats.	2001 Apr	11311893
[(35)S]GTPgammaS autoradiography reveals a wide distribution of G(i/o)-linked ADP receptors in the nervous system: close similarities with the platelet P2Y(ADP) receptor.	2001 Apr	11299313
AMP-activated protein kinase is highly expressed in neurons in the developing rat brain and promotes neuronal survival following glucose deprivation.	2001 Aug	11665862
Control of the proinflammatory state in cystic fibrosis lung epithelial cells by genes from the TNF-alphaR/NFkappaB pathway.	2001 Aug	11591888
Allosteric adenosine modulation to reduce allodynia.	2001 Aug	11506115
Isoflurane-induced protection against myocardial stunning is independent of adenosine 1 (A(1)) receptor in isolated rat heart.	2001 Aug	11493499
Adenosine A3 agonist cardioprotection in isolated rat and rabbit hearts is blocked by the A1 antagonist DPCPX.	2001 Aug	11454590
Adenosine receptor antagonists cancelled the ischemic tolerance phenomenon in gerbil.	2001 Aug 10	11489258
Adenosine A1 receptors reduce release from excitatory but not inhibitory synaptic inputs onto lateral horn neurons.	2001 Aug 15	11487654
Adenosine A(1) receptor agonism in the immature rat brain and heart.	2001 Aug 31	11527543
Adenosine inhibits glutamate exocytosis largely without interfering with Ca2+ influx in rat cerebrocortical synaptosomes.	2001 Aug 31	11514071
Antagonism of adenosine A(1) receptors in the NTS does not affect the chemoreflex in awake rats.	2001 Dec	11705794
Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors.	2001 Dec	11704566
Activation of presynaptic A1-receptors by endogenous adenosine inhibits acetylcholine release in the guinea-pig ileum.	2001 Feb	11422576
Adenosine A(1) and A(2A) receptors modulate sleep state and breathing in fetal sheep.	2001 Jul	11408450
Modulation of ethanol-induced motor incoordination by mouse striatal A(1) adenosinergic receptor.	2001 Jul 1	11543952
Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine.	2001 Jul 6	11487090
Inhibition of calcium channels by opioid- and adenosine-receptor agonists in neurons of the nucleus accumbens.	2001 Jun	11375249
Adenosine A(1) receptor-mediated inhibition of protein kinase A-induced calcitonin gene-related peptide release from rat trigeminal neurons.	2001 Jun	11353815
Poly(lactic acid) microspheres for the sustained release of a selective A1 receptor agonist.	2001 Jun 15	11516507
Agonist-stimulated [35S]GTPgammaS autoradiography: optimization for high sensitivity.	2001 Jun 22	11430907
Involvement of the cerebellar adenosine A(1) receptor in cannabinoid-induced motor incoordination in the acute and tolerant state in mice.	2001 Jun 29	11423093
Reduced PO(2) and adenosine formation preserve arteriolar nitric oxide synthesis during sympathetic constriction in the rat intestine.	2001 Mar-Apr	11316946
Electrically evoked release of glutamate in rat hippocampal slices: effects of various drugs and fimbria-fornix lesions.	2001 May	11383708
Ameliorative effects of paeoniflorin, a major constituent of peony root, on adenosine A1 receptor-mediated impairment of passive avoidance performance and long-term potentiation in the hippocampus.	2001 May	11379768
Age-dependent decrease in adenosine A1 receptor binding sites in the rat brain. Effect of cis unsaturated free fatty acids.	2001 May	11358511
Determination of amino acid residues that are accessible from the ligand binding crevice in the seventh transmembrane-spanning region of the human A(1) adenosine receptor.	2001 May	11306703
Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease.	2001 May 15	11319241
Effect of adenosine receptor blockade on pial arteriolar dilation during sciatic nerve stimulation.	2001 Nov	11668063
Modulation of N-type Ca2+ currents by A1-adenosine receptor activation in male rat pelvic ganglion neurons.	2001 Nov	11602660
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.	2001 Nov	11600438
Acute and chronic caffeine administration differentially alters striatal gene expression in wild-type and adenosine A(2A) receptor-deficient mice.	2001 Nov	11574941
Activation of synaptic NMDA receptors by action potential-dependent release of transmitter during hypoxia impairs recovery of synaptic transmission on reoxygenation.	2001 Nov 1	11606644
Solubilisation and immunoprecipitation of rat striatal adenosine A(2A) receptors.	2001 Nov 16	11728423
Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats.	2001 Oct	11700012
Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO.	2001 Oct	11606314
Neuronal mechanisms of the anoxia-induced network oscillations in the rat hippocampus in vitro.	2001 Oct 15	11600686
Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia.	2001 Sep	11564652
Systemic adenosine given after ischemia protects renal function via A(2a) adenosine receptor activation.	2001 Sep	11532695
Inhibitory effect of ischemic preconditioning on leukocyte participation in retinal ischemia-reperfusion injury.	2001 Sep	11527953
The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells.	2001 Sep	11522602
Adenosine-mediated inhibition of striatal GABAergic synaptic transmission during in vitro ischaemia.	2001 Sep	11522587
Adenosine linking reduced O2 to arteriolar NO release in intestine is not formed from extracellular ATP.	2001 Sep	11514287
Amp 579 reduces contracture and limits infarction in rabbit heart by activating adenosine A2 receptors.	2001 Sep	11486252
Effects of angiotensin III and angiotensin IV on pentylenetetrazol seizure susceptibility (threshold and kindling): interaction with adenosine A(1) receptors.	2001 Sep 15	11704344
Smooth muscle does not have a common P2x receptor phenotype: expression, ontogeny and function of P2x1 receptors in mouse ileum, bladder and reproductive systems.	2001 Sep 17	11570704

Patents

Sample Use Guides

In Vivo Use Guide

Mice: * 3 µg intrathecally * 1, 3, 6 mg/kg systemic administration (i.p.) Rats: 100 ug/kg intravenous

Route of Administration: Other

In Vitro Use Guide

The effects of the A1 adenosine receptor antagonist 1,3-dipropyl-8-cyclopentylxanthine (DPCPX) on force of contraction were examined in isolated electrically driven auricles and papillary muscles from guinea-pigs in the absence and presence of (-)-N6-phenylisopropyladenosine (PIA) and 5'-N-ethylcarboxamidadenosine (NECA). In auricles DPCPX (30-1000 mmol/l) alone increased force of contraction.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:57 GMT 2025`
Record UNII	9PTP4FOI9E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PD-116948

Preferred Name

English

8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE

Systematic Name

English

1,3-DIPROPYL-8-CYCLOPENTYLXANTHINE

Systematic Name

English

1H-PURINE-2,6-DIONE, 8-CYCLOPENTYL-3,9-DIHYDRO-1,3-DIPROPYL-

Systematic Name

English

CPX

Common Name

English

DPCPX

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

103997