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C8031

Sigma-Aldrich

N6-Cyclopentyladenosine

solid

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Synonym(s):
CPA
Empirical Formula (Hill Notation):
C15H21N5O4
CAS Number:
Molecular Weight:
335.36
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

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

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1 of 4

This Item
A6563C7938A6566
vibrant-m

C8031

N6-Cyclopentyladenosine

vibrant-m

A6563

6-Anilinoquinoline-5,8-quinone

vibrant-m

C7938

2-Chloro-N6-cyclopentyladenosine

vibrant-m

A6566

2-Hydroxysaclofen

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

solubility

H2O: 1.7 mg/mL, DMSO: 23 mg/mL, 0.1 M HCl: 12 mg/mL

solubility

0.1 M HCl: 1 mg/mL, methanol: 11 mg/mL, ethanol: 8 mg/mL

solubility

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

solubility

H2O: 1 mg/mL, 0.1 M HCl: 1.2 mg/mL, methanol: 1.4 mg/mL, DMSO: 28 mg/mL, 0.1 M NaOH: 9.5 mg/mL

color

white to off-white

color

violet

color

-

color

white

Gene Information

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

Gene Information

-

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Gene Information

human ... GABBR1(2550), GABBR2(9568)

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

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)


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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
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
Solid lipid microparticles for the stability enhancement of the polar drug N6-cyclopentyladenosine
Dalpiaz A, et al.
International Journal of Pharmaceutics, 355(1-2), 81-86 (2008)
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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