Dipropylcyclopentylxanthine

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX, PD-116,948) is a drug which acts as a potent and selective antagonist for the adenosine A₁ receptor.^[1][2] It has high selectivity for A₁ over other adenosine receptor subtypes, but as with other xanthine derivatives DPCPX also acts as a phosphodiesterase inhibitor, and is almost as potent as rolipram at inhibiting PDE4.^[3] It has been used to study the function of the adenosine A₁ receptor in animals,^[4][5] which has been found to be involved in several important functions such as regulation of breathing^[6] and activity in various regions of the brain,^[7][8] and DPCPX has also been shown to produce behavioural effects such as increasing the hallucinogen-appropriate responding produced by the 5-HT_2A agonist DOI,^[9] and the dopamine release induced by MDMA,^[10] as well as having interactions with a range of anticonvulsant drugs.^[11][12]

Dipropylcyclopentylxanthine

Clinical data
ATC code	None
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 8-cyclopentyl-1,3-dipropyl-7H-purine-2,6-dione
CAS Number	102146-07-6 N
PubChem CID	1329
IUPHAR/BPS	386
ChemSpider	1289 Y
UNII	9PTP4FOI9E
ChEBI	CHEBI:73282 N
ChEMBL	ChEMBL183 Y
CompTox Dashboard (EPA)	DTXSID50144706
ECHA InfoCard	100.162.425
Chemical and physical data
Formula	C16H24N4O2
Molar mass	304.394 g·mol−1
3D model (JSmol)	Interactive image
Melting point	191 to 194 °C (376 to 381 °F)
SMILES CCCn3c(=O)c2nc(C1CCCC1)[nH]c2n(CCC)c3=O
InChI InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18) Y Key:FFBDFADSZUINTG-UHFFFAOYSA-N Y
NY (what is this?)  (verify)