Chemistry:Dipropylcyclopentylxanthine

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Short description: Chemical compound
Dipropylcyclopentylxanthine
Skeletal formula of dipropylcyclopentylxanthine
Space-filling model of the dipropylcyclopentylxanthine molecule
Clinical data
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC16H24N4O2
Molar mass304.394 g·mol−1
3D model (JSmol)
Melting point191 to 194 °C (376 to 381 °F)
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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-HT2A agonist DOI,[9] and the dopamine release induced by MDMA,[10] as well as having interactions with a range of anticonvulsant drugs.[11][12]

See also

References

  1. "Potent adenosine receptor antagonists that are selective for the A1 receptor subtype". Molecular Pharmacology 31 (3): 247–52. March 1987. PMID 3561384. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=3561384. 
  2. "8-Cyclopentyl-1,3-dipropylxanthine (DPCPX)--a selective high affinity antagonist radioligand for A1 adenosine receptors". Naunyn-Schmiedeberg's Archives of Pharmacology 336 (2): 204–10. August 1987. doi:10.1007/BF00165806. PMID 2825043. 
  3. "Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes". Biochemical Pharmacology 45 (4): 847–51. February 1993. doi:10.1016/0006-2952(93)90168-V. PMID 7680859. 
  4. "1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists?". General Pharmacology 25 (3): 387–94. May 1994. doi:10.1016/0306-3623(94)90185-6. PMID 7926579. 
  5. "Progress in the pursuit of therapeutic adenosine receptor antagonists". Medicinal Research Reviews 26 (2): 131–59. March 2006. doi:10.1002/med.20048. PMID 16380972. 
  6. "Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation". BMC Neuroscience 9: 95. 2008. doi:10.1186/1471-2202-9-95. PMID 18826652. 
  7. "Activation of adenosine A1 receptor-induced neural stem cell proliferation via MEK/ERK and Akt signaling pathways". Journal of Neuroscience Research 86 (13): 2820–8. October 2008. doi:10.1002/jnr.21742. PMID 18618669. 
  8. "Adenosine as an endogenous regulating factor of hippocampal sharp waves". Hippocampus 19 (2): 205–20. February 2009. doi:10.1002/hipo.20497. PMID 18785213. 
  9. "Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats". Neuropharmacology 56 (8): 1082–7. March 2009. doi:10.1016/j.neuropharm.2009.03.005. PMID 19324062. 
  10. "A role for adenosine A(1) receptor blockade in the ability of caffeine to promote MDMA "Ecstasy"-induced striatal dopamine release". European Journal of Pharmacology 650 (1): 220–8. January 2011. doi:10.1016/j.ejphar.2010.10.012. PMID 20951694. 
  11. "Repeated treatment with adenosine A1 receptor agonist and antagonist modifies the anticonvulsant properties of CPPene". European Journal of Pharmacology 317 (2–3): 239–45. December 1996. doi:10.1016/S0014-2999(96)00746-7. PMID 8997606. 
  12. "[Influence of the antagonist of adenosine A1 receptors, 8-cyclopentyl-1 ,3-dipropylxanthine, upon the anticonvulsant activity of antiepileptic drugs in mice]" (in pl). Przegla̧d Lekarski 65 (11): 759–63. 2008. PMID 19205356.