C7938

2-Chloro-N⁶-cyclopentyladenosine

adenosine receptor agonist

• Synonym(s): CCPA
• Empirical Formula (Hill Notation): C₁₅H₂₀ClN₅O₄
• CAS Number: 37739-05-2
• Molecular Weight: 369.80
• MDL number: MFCD00078574
• UNSPSC Code: 41106305
• PubChem Substance ID: 24892583
• NACRES: NA.51

Properties

• Quality Level: 200
• assay: ≥98% (TLC)
• form: powder
• solubility: methanol: 19.60-20.40 mg/mL, clear, colorless to faintly yellow
• storage temp.: 2-8°C
• SMILES string: OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCC4)nc(Cl)nc23
• InChI: 1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1
• InChI key: XSMYYYQVWPZWIZ-IDTAVKCVSA-N
• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140) ; rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Description

Application

2-Chloro-N6-cyclopentyladenosine (CCPA) may be used as an A1 adenosine receptor agonist with high selectivity. CCPA is often used with other adenosine receptor agonists and antagonist to resolve A(1), A(2A) and A(3) receptor functions. These include DPCPX (A(1) receptor antagonist), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-α][1,3,5]triazin-5-ylamino]ethyl)phenol (A(2A) receptor antagonist), and 4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid hydrochloride (A(2A) receptor agonist), and Cl-IB-MECA, (A(3)) receptor agonist).

Biochem/physiol Actions

A₁ adenosine receptor agonist with high selectivity: reportedly 10,000-fold for A₁ over A₂ receptors.

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)