Structure via PubChem · Public domain (PubChem)
cyclopentyladenosine
Sign in to saveAlso known as CPA, N(6)-cyclopentyladenosine, N6-cyclopentyladenosine
'''N6-Cyclopentyladenosine (CPA''') is a drug which acts as a selective adenosine A1 receptor agonist. It has mainly cardiovascular effects with only subtle alterations of behavior. CPA is widely used in scientific research into the adenosine receptors and has been used to derive a large family of derivatives.
Chemical data
- Formula
- C15H21N5O4
- Molecular weight
- 335.36 g/mol
- IUPAC name
- (2R,3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
- SMILES
- C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
- InChIKey
- SQMWSBKSHWARHU-SDBHATRESA-N
- XLogP
- 0.9
- Polar surface area
- 126 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,289 papers- Cyclopentyladenosine-induced homologous down-regulation of A1 adenosine receptors (A1AR) in intact neurons is accompanied by receptor sequestration but not a reduction in A1AR mRNA expression or G protein alpha-subunit content.Journal of neurochemistry · 1998
- Adenosine modulates alpha2-adrenergic receptors within specific subnuclei of the nucleus tractus solitarius in normotensive and spontaneously hypertensive rats.Hypertension research : official journal of the Japanese Society of Hypertension · 2008
- 2-Chloro-N6-cyclopentyladenosine: a highly selective agonist at A1 adenosine receptors.Naunyn-Schmiedeberg's archives of pharmacology · 1988
- Cyclopentyladenosine improves cell proliferation, wound healing, and hair growth.The Journal of surgical research · 1999
- Adenosine A1 Receptor Agonist 2-chloro-N6-cyclopentyladenosine and Hippocampal Excitability During Brain Development in Rats.Frontiers in pharmacology · 2019
via PubMed
Wikidata facts
- Mass
- 335.159
Show 4 more facts
- chemical formula
- C₁₅H₂₁N₅O₄
- isomeric SMILES
- C1CCC(C1)NC2=NC=NC3=C2N=CN3[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
- canonical SMILES
- C1CCC(C1)NC2=NC=NC3=C2N=CN3C4C(C(C(O4)CO)O)O
- Commons category
- N6-Cyclopentyladenosine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
'''N6-Cyclopentyladenosine (CPA') is a drug which acts as a selective adenosine A1 receptor agonist. It has mainly cardiovascular effects with only subtle alterations of behavior. CPA is widely used in scientific research into the adenosine receptors and has been used to derive a large family of derivatives.
== See also == N''6-Methyladenosine
Excerpted from Wikipedia’s “cyclopentyladenosine” article, available under the CC BY-SA 4.0 licence.