41552-82-3

Basic information

• Product Name: N6-CYCLOPENTYLADENOSINE
• Synonyms: N6-CYCLOPENTYLADENOSINE;N-CYCLOPENTYLADENOSINE;N(sup 6)-cyclopentyladenosine;Adenosine, N-cyclopentyl-;N6-Cyclopentyladenosine,CPA;(2R,3R,4S,5R)-2-(6-(CyclopentylaMino)-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;N6-Cyclopentyladenosine
• CAS NO: 41552-82-3
• Molecular Formula: C₁₅H₂₁N₅O₄
• Molecular Weight: 335.36
• Product Categories: Adenosine receptor
• Mol File: 41552-82-3.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 673.4 °C at 760 mmHg
• Flash Point: 361.1 °C
• Appearance: white to off-white/
• Density: 1.78 g/cm³
• Vapor Pressure: 4.71E-19mmHg at 25°C
• Refractive Index: 1.816
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble1.7mg/mL
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: N6-CYCLOPENTYLADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N6-CYCLOPENTYLADENOSINE(41552-82-3)
• EPA Substance Registry System: N6-CYCLOPENTYLADENOSINE(41552-82-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 41552-82-3(Hazardous Substances Data)

Usage

Description

N6-Cyclopentyladenosine is a selective Adenosine A1-R agonist, characterized by its Ki values of 2.3, 790, and 43 nM for human A1, A2A, and A3 receptors, respectively. It also exhibits an EC50 value of 18600 nM for hA2B. N6-Cyclopentyladenosine has demonstrated efficacy against organophosphate toxicity and has been utilized in various research applications.

Uses

Used in Pharmaceutical Applications:
N6-Cyclopentyladenosine is used as a selective agonist for studying the effects on adenosine receptors, particularly A1, A2A, and A3 receptors. Its application in this field aids in understanding the role of these receptors in various physiological processes and potential therapeutic interventions.
Used in Organophosphate Toxicity Research:
N6-Cyclopentyladenosine is used as a therapeutic agent for studying its efficacy against organophosphate toxicity. This application helps in exploring potential treatments for poisoning caused by organophosphate compounds.
Used in Smooth Muscle Cell Research:
N6-Cyclopentyladenosine is used as a research tool to study its effects on cavernosal smooth muscle cells from lean and db/db (obesity and type II diabetes caused by a leptin receptor mutation) mice. This application contributes to the understanding of the compound's impact on smooth muscle cell function in the context of obesity and type II diabetes.

Biological Activity

Potent and selective adenosine A 1 receptor agonist (K i values are 2.3, 790 and 43 nM for human A 1 , A 2A and A 3 receptors respectively; EC 50 = 18600 nM for hA 2B ). Centrally active following systemic administration in vivo .

Biochem/physiol Actions

N6-Cyclopentyladenosine (CPA) is an adenosine derivative and a potent A1 adenosine receptor agonist. It acts as an anticonvulsant and might exhibit protective actions against aminophylline (AMPH)-induced seizures.

InChI:InChI=1/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 1003-03-8 Cyclopentamine 
• 1229622-80-3 C₄₂H₄₇N₅O₆ 
• 58-61-7 adenosine 
• 14426-53-0 6-Iodo-purine riboside 
• 64344-19-0 N⁶-chloro-adenosine 
• 37739-05-2 2-chloro-N⁶-cyclopentyladenosine 
• 3056-18-6 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 

Downstream Products

• 871108-05-3 ((2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate 
• 151563-25-6 Carbonic acid benzyl ester (3aR,4R,6R,6aR)-6-(6-cyclopentylamino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 199587-01-4 5'-tosyl-2',3'-di-O-benzoyl-N⁶-cyclopentyladenosine 
• 199587-00-3 2',3'-di-O-benzoyl-N⁶-cyclopentyladenosine 
• 197796-86-4 (2R,3R,4R,5S)-4-Azido-2-(6-cyclopentylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol 
• 581106-44-7 Cyclopentyl-{9-[(3aR,4R,6S,6aS)-6-(2-fluoro-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-amine 
• 365533-71-7 3,4,5-trimethoxy-benzoic acid 6-(6-cyclopentylamino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 

Relevant articles and documents

First no-carrier-added radioselenation of an adenosine-A1 receptor ligand

The precursor synthesis and the no-carrier-added (n.c.a.) radiosynthesis of the adenosine-A1 receptor ligand 5′-(methyl[ 75Se]seleno)-N6-cyclopentyladenosine ([75Se]1) are described in this report. A method was developed starting from elemental n.c.a. selenium-75, followed by a three-step polymer-supported radioselenation and deprotection which gave the radioligand with a radiochemical yield of 30%, a radiochemical purity of > 99% and a specific radioactivity of > 300 GBq/mmol (8 Ci/mmol). Preparation time was 40 min. The nonradioactive compound 5′-(methylseleno)-N6-cyclopentyladenosine (1) was pharmacologically evaluated in vitro and showed high affinity and selectivity for the adenosine-A1 receptor. These preliminary results suggest that this compound could be a useful radioligand for the noninvasive imaging of the brain adenosine-A1 receptors using positron emission tomography (PET) when labelled with the positron emitter selenium-73 (half-life: 7.1 h). Copyright

METHODS OF PREVENTING, REDUCING OR TREATING MACULAR DEGENERATION

The present invention is directed to selective adenosine A1 agonist compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, reduce or prevent age-related macular degeneration.

OPHTHALMIC FORMULATIONS

The present invention relates to an ophthalmic formulation which comprises a fine particle of Compound A in an aqueous suspension and a manufacturing process thereof. More specifically, the present invention relates to a topically applied ophthalmic aqueous suspension which is obtainable by suspending fine particles of Compound A in an aqueous vehicle containing a surfactant and boric acid. The invention also provides processes for making the ophthalmic formulations and to methods of use thereof.