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Merck

C8031

N6-Cyclopentyladenosine

solid

Sinónimos:

CPA

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About This Item

Fórmula empírica (notación de Hill):
C15H21N5O4
Número CAS:
41552-82-3
Peso molecular:
335.36
NACRES:
NA.77
PubChem Substance ID:
24277686
UNSPSC Code:
12352200
MDL number:
MFCD00036845

Nombre del producto

N6-Cyclopentyladenosine, solid

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

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCC4)ncnc23

InChI key

SQMWSBKSHWARHU-SDBHATRESA-N

form

solid

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

Quality Level

200
500

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA3(140)
mouse ... Adora1(11539)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

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Categorías relacionadas

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

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000113392
038M4058V
105M4130V
076M4127V
13141214

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Ainhoa Bilbao et al.
Addiction biology, 24(5), 1008-1018 (2019-06-27)
The co-occurrence of chronic pain and alcohol use disorders (AUDs) involves complex interactions between genetic and neurophysiological aspects, and the research has reported mixed findings when they both co-occur. There is also an indication of a gender-dependent effect; males are
Yahaira Naaldijk et al.
BMC biotechnology, 16(1), 85-85 (2016-12-03)
Preservation of human skin fibroblasts and keratinocytes is essential for the creation of skin tissue banks. For successful cryopreservation of cells, selection of an appropriate cryoprotectant agent (CPA) is imperative. The aim of this study was to identify CPAs that
Individual and combined effects of N6-cyclopentyladenosine, flunarizine and diazepam on aminophylline-induced recurrent generalized seizures in mice
Jaishree J, et al.
Polish Journal of Pharmacology, 55(4), 559-564 (2003)
Cheng-Hui Hsiao et al.
Biomedical chromatography : BMC, 33(9), e4518-e4518 (2019-02-26)
The prominent stromal compartment surrounds pancreatic ductal adenocarcinoma and protects the tumor cells from chemo- or radiotherapy. We hypothesized that our nano formulation carrying cyclopamine (CPA, stroma modulator) and paclitaxel (PTX, antitumor agent) could increase the permeation of PTX through
Claudia Iasillo et al.
Nucleic acids research, 45(17), 10229-10241 (2017-10-04)
Termination of transcription is important for establishing gene punctuation marks. It is also critical for suppressing many of the pervasive transcription events occurring throughout eukaryotic genomes and coupling their RNA products to efficient decay. In human cells, the ARS2 protein
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