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C7938

2-Chloro-N⁶-cyclopentyladenosine

Name: 2-Chloro-N<SUP>6</SUP>-cyclopentyladenosine
Brand: SIGMA

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

NACRES:

NA.51

PubChem Substance ID:

24892583

UNSPSC Code:

41106305

MDL number:

MFCD00078574

Assay:

≥98% (TLC)

Form:

powder

Solubility:

methanol: 19.60-20.40 mg/mL, clear, colorless to faintly yellow

Storage temp.:

2-8°C

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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A prominent role for the IL1 pathway and IL15 in susceptibility to chronic cavitary pulmonary aspergillosis.

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)

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Journal of medicinal chemistry, 51(18), 5875-5879 (2008-08-30)

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Despite decades of research and thousands of experimental publications, acute preconditioning strategies have yet to be implemented in clinical practice. While some have attributed this to a failure of the experimental studies to mimic the clinical environment, others have suggested

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Journal of molecular medicine (Berlin, Germany), 96(10), 1049-1060 (2018-08-09)

Osteoarthritis (OA), the most common form of arthritis, is characterized by inflammation of joints and cartilage degradation leading to disability, discomfort, severe pain, inflammation, and stiffness of the joint. It has been shown that adenosine, a purine nucleoside composed of

Inhibition of Adenosine Pathway Alters Atrial Electrophysiology and Prevents Atrial Fibrillation.

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

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Global Trade Item Number

SKU	GTIN
C7938-25MG	04061833047712
C7938-10MG	04061833521380

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