Dipropylcyclopentylxanthine: Difference between revisions

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{{drugbox |
#REDIRECT [[Adenosine receptor#Antagonism and agonism]]
| IUPAC_name = 8-Cyclopentyl-1,3-dipropylxanthine
| image = 8-Cyclopentyl-1,3-dipropylxanthine.png
| width = 240
| CAS_number = 102146-07-6
| synonyms = DPCPX
| ATC_prefix =
| ATC_suffix =
| PubChem =
| DrugBank =
| C = 16 | H = 24 | N = 4 | O = 2
| molecular_weight = 304.386 g/mol
| smiles = C3CCCC3c(nc2c1=O)nc2n(CCC)c(=O)n1CCC
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- Schedule I -->
| legal_UK = <!-- Class A -->
| legal_US =
| legal_status = legal
| routes_of_administration =
}}

'''8-Cyclopentyl-1,3-dipropylxanthine''' ('''DPCPX''') is a drug which acts as a potent and selective antagonist for the [[Adenosine A1 receptor]].<ref>{{cite journal | author = Martinson EA, Johnson RA, Wells JN | title = Potent adenosine receptor antagonists that are selective for the A1 receptor subtype | journal = Molecular Pharmacology | volume = 31 | issue = 3 | pages = 247–52 | year = 1987 | month = March | pmid = 3561384 | doi = | url = http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=3561384 | issn = }}</ref><ref>{{cite journal | author = Lohse MJ, Klotz KN, Lindenborn-Fotinos J, Reddington M, Schwabe U, Olsson RA | title = 8-Cyclopentyl-1,3-dipropylxanthine (DPCPX)--a selective high affinity antagonist radioligand for A1 adenosine receptors | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 336 | issue = 2 | pages = 204–10 | year = 1987 | month = August | pmid = 2825043 | doi = | url = | issn = }}</ref> It has been used to study the function of the adenosine A1 receptor in animals,<ref>{{cite journal | author = Coates J, Sheehan MJ, Strong P | title = 1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists? | journal = General Pharmacology | volume = 25 | issue = 3 | pages = 387–94 | year = 1994 | month = May | pmid = 7926579 | doi = | url = | issn = }}</ref><ref>{{cite journal | author = Moro S, Gao ZG, Jacobson KA, Spalluto G | title = Progress in the pursuit of therapeutic adenosine receptor antagonists | journal = Medicinal Research Reviews | volume = 26 | issue = 2 | pages = 131–59 | year = 2006 | month = March | pmid = 16380972 | doi = 10.1002/med.20048 | url = | issn = }}</ref> which has been found to be involved in several important functions such as regulation of breathing<ref>{{cite journal | author = Vandam RJ, Shields EJ, Kelty JD | title = Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation | journal = BMC Neuroscience | volume = 9 | issue = | pages = 95 | year = 2008 | pmid = 18826652 | pmc = 2567986 | doi = 10.1186/1471-2202-9-95 | url = | issn = }}</ref> and activity in various regions of the brain,<ref>{{cite journal | author = Migita H, Kominami K, Higashida M, Maruyama R, Tuchida N, McDonald F, Shimada F, Sakurada K | title = Activation of adenosine A1 receptor-induced neural stem cell proliferation via MEK/ERK and Akt signaling pathways | journal = Journal of Neuroscience Research | volume = 86 | issue = 13 | pages = 2820–8 | year = 2008 | month = October | pmid = 18618669 | doi = 10.1002/jnr.21742 | url = | issn = }}</ref><ref>{{cite journal | author = Wu C, Wong T, Wu X, Sheppy E, Zhang L | title = Adenosine as an endogenous regulating factor of hippocampal sharp waves | journal = Hippocampus | volume = 19 | issue = 2 | pages = 205–20 | year = 2009 | month = February | pmid = 18785213 | doi = 10.1002/hipo.20497 | url = | issn = }}</ref> as well as having behavioural effects such as increasing the hallucinogen-appropriate responding produced by the [[5-HT2A receptor|5-HT<sub>2A</sub>]] agonist [[2,5-Dimethoxy-4-iodoamphetamine|DOI]].<ref>{{cite journal | author = Marek GJ | title = Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats | journal = Neuropharmacology | volume = | issue = | pages = | year = 2009 | month = March | pmid = 19324062 | doi = 10.1016/j.neuropharm.2009.03.005 | url = | issn = }}</ref>



==References==
{{reflist}}

Revision as of 02:40, 18 April 2009

Dipropylcyclopentylxanthine
Clinical data
Other namesDPCPX
Legal status
Legal status
  • In general: legal
Identifiers
  • 8-Cyclopentyl-1,3-dipropylxanthine
CAS Number
CompTox Dashboard (EPA)
ECHA InfoCard100.162.425 Edit this at Wikidata
Chemical and physical data
FormulaC16H24N4O2
Molar mass304.386 g/mol g·mol−1
3D model (JSmol)
  • C3CCCC3c(nc2c1=O)nc2n(CCC)c(=O)n1CCC

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a drug which acts as a potent and selective antagonist for the Adenosine A1 receptor.[1][2] It has been used to study the function of the adenosine A1 receptor in animals,[3][4] which has been found to be involved in several important functions such as regulation of breathing[5] and activity in various regions of the brain,[6][7] as well as having behavioural effects such as increasing the hallucinogen-appropriate responding produced by the 5-HT2A agonist DOI.[8]


References

  1. ^ Martinson EA, Johnson RA, Wells JN (1987). "Potent adenosine receptor antagonists that are selective for the A1 receptor subtype". Molecular Pharmacology. 31 (3): 247–52. PMID 3561384. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Lohse MJ, Klotz KN, Lindenborn-Fotinos J, Reddington M, Schwabe U, Olsson RA (1987). "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. PMID 2825043. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Coates J, Sheehan MJ, Strong P (1994). "1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists?". General Pharmacology. 25 (3): 387–94. PMID 7926579. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Moro S, Gao ZG, Jacobson KA, Spalluto G (2006). "Progress in the pursuit of therapeutic adenosine receptor antagonists". Medicinal Research Reviews. 26 (2): 131–59. doi:10.1002/med.20048. PMID 16380972. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ Vandam RJ, Shields EJ, Kelty JD (2008). "Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation". BMC Neuroscience. 9: 95. doi:10.1186/1471-2202-9-95. PMC 2567986. PMID 18826652.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  6. ^ Migita H, Kominami K, Higashida M, Maruyama R, Tuchida N, McDonald F, Shimada F, Sakurada K (2008). "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. doi:10.1002/jnr.21742. PMID 18618669. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  7. ^ Wu C, Wong T, Wu X, Sheppy E, Zhang L (2009). "Adenosine as an endogenous regulating factor of hippocampal sharp waves". Hippocampus. 19 (2): 205–20. doi:10.1002/hipo.20497. PMID 18785213. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. ^ Marek GJ (2009). "Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats". Neuropharmacology. doi:10.1016/j.neuropharm.2009.03.005. PMID 19324062. {{cite journal}}: Unknown parameter |month= ignored (help)
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