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Merck

C8031

N6-Cyclopentyladenosine

solid

Synonym(s):

CPA

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About This Item

Empirical Formula (Hill Notation):
C15H21N5O4
CAS Number:
41552-82-3
Molecular Weight:
335.36
NACRES:
NA.77
PubChem Substance ID:
24277686
UNSPSC Code:
12352200
MDL number:
MFCD00036845

Key Documents

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Product Name

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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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

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

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Andi Hermansyah et al.
PloS one, 12(9), e0184954-e0184954 (2017-09-19)
Community pharmacy practice in Australia is changing and Research and Development (R&D) in community pharmacy plays an important role in contributing to the changes. A range of Cognitive Pharmacy Services (CPS) were developed from R&D programs, yet their implementation has
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)
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)
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
Van Tran et al.
Biophysical journal, 115(7), 1344-1356 (2018-08-15)
Not only the amplitude but also the time course of a presynaptic Ca2+ transient determine multiple aspects of synaptic transmission. In small bouton-type synapses, the mechanisms underlying the Ca2+ decay kinetics have not been fully investigated. Here, factors that shape
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