C8031

N⁶-Cyclopentyladenosine

solid

• Synonym(s): CPA
• Empirical Formula (Hill Notation): C₁₅H₂₁N₅O₄
• CAS Number: 41552-82-3
• Molecular Weight: 335.36
• MDL number: MFCD00036845
• UNSPSC Code: 12352200
• PubChem Substance ID: 24277686
• NACRES: NA.77

Properties

• form: solid
• Quality Level: 200
• color: white to off-white
• solubility: H₂O: 1.7 mg/mL; 0.1 M HCl: 12 mg/mL; DMSO: 23 mg/mL
• storage temp.: 2-8°C
• SMILES string: OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCC4)ncnc23
• InChI: 1S/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
• InChI key: SQMWSBKSHWARHU-SDBHATRESA-N
• Gene Information: human ... ADORA1(134) , ADORA2A(135) , ADORA3(140) ; mouse ... Adora1(11539) ; rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Description

Application

N⁶-Cyclopentyladenosine has also been used to study its effect on p53 and caspase 3, 8, and 9 expression and apoptosis rate in MCF-7 breast cancer cell line.

N⁶-Cyclopentyladenosine has been used to study its effect on the cavernosal smooth muscle cells from lean and db/db (obesity and type II diabetes caused by a leptin receptor mutation) mice.

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.

N⁶-Cyclopentyladenosine also exhibits analgesic effect against acute, arthritis-induced and neuropathic pain.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Physical form

hygroscopic solid

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)