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C8031 Sigma-Aldrich

N6-Cyclopentyladenosine

solid

Synonym: CPA

  • CAS Number 41552-82-3

  • Empirical Formula (Hill Notation) C15H21N5O4

  • Molecular Weight 335.36

  •  MDL number MFCD00036845

  •  PubChem Substance ID 24277686

  •  NACRES NA.77

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Properties

Related Categories Adenosines/P2 Nucleotide Receptor - Agonists, Adenosines/P2 Nucleotide Receptors (Purinergics), Agonists, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   200
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
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
Gene Information   human ... ADORA1(134), ADORA2A(135), ADORA3(140)
mouse ... Adora1(11539)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Description

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.

Packaging

100 mg in glass bottle

25 mg in poly bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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