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C7938

Sigma-Aldrich

2-Chloro-N6-cyclopentyladenosine

adenosine receptor agonist

Synonym(s):

CCPA

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About This Item

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

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)

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Romeo Romagnoli et al.
Journal of medicinal chemistry, 51(18), 5875-5879 (2008-08-30)
The synthesis and evaluation of a series of 2-amino-3-(4-chlorobenzoyl)-4-[4-(alkyl/aryl)piperazin-yl]thiophene derivatives as allosteric enhancers of the A 1-adenosine receptor are described. The nature of substituents on the phenyl ring tethered to the piperazine seem to exert a fundamental influence on the
Iftikhar Ahmad et al.
Scientific reports, 10(1), 364-364 (2020-01-17)
Real world complex networks are indirect representation of complex systems. They grow over time. These networks are fragmented and raucous in practice. An important concern about complex network is link prediction. Link prediction aims to determine the possibility of probable
N L D Smith et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 20(8), O480-O488 (2013-11-28)
Chronic cavitary pulmonary aspergillosis (CCPA) is a progressive lung condition with a 10-30% annual mortality. Although overtly immunocompetent, some immunogenetic defect in patients is likely. To investigate a possible immunogenetic defect in CCPA, we analysed biologically plausible candidate genes in
Luca Soattin et al.
Frontiers in physiology, 11, 493-493 (2020-07-01)
Adenosine leads to atrial action potential (AP) shortening through activation of adenosine 1 receptors (A1-R) and subsequent opening of G-protein-coupled inwardly rectifying K+ channels. Extracellular production of adenosine is drastically increased during stress and ischemia. The aim of this study
Ellen V Langemeijer et al.
Purinergic signalling, 9(1), 91-100 (2012-10-12)
The concept of functional selectivity offers great potential for the development of drugs that selectively activate a specific intracellular signaling pathway. During the last few years, it has become possible to systematically analyse compound libraries on G protein-coupled receptors (GPCRs)
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