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CGS-21680

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CGS-21680
Names
IUPAC name
3-[4-(2-{[6-Amino-9-(N-ethyl-β-D-ribofuranosyluronamide)-9H-purin-2-yl]amino}ethyl)phenyl]propanoic acid
Systematic IUPAC name
3-{4-[2-({6-Amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}amino)ethyl]phenyl}propanoic acid
Other names
CGS 21680
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C23H29N7O6/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29)/t16-,17+,18-,22+/m0/s1 ☒N
    Key: PAOANWZGLPPROA-RQXXJAGISA-N ☒N
  • InChI=1/C23H29N7O6/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29)/t16-,17+,18-,22+/m0/s1
    Key: PAOANWZGLPPROA-RQXXJAGIBL
  • O=C(O)CCc1ccc(cc1)CCNc2nc(c3ncn(c3n2)[C@@H]4O[C@H](C(=O)NCC)[C@@H](O)[C@H]4O)N
Properties
C23H29N7O6
Molar mass 499.52
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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CGS-21680 is a specific adenosine A2A subtype receptor agonist. It is usually presented as an organic hydrochloride salt with a molecular weight of 536.0 g/M. It is soluble up to 3.4 mg/mL in DMSO and 20 mg/mL in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin.

The chemical is currently used by researchers interested in studying neuronal transmission with a high-affinity, subtype specific analogue for adenosine. This includes research in respiration where it is believed that A2A receptors are involved in rhythm generation in the pre-Bötzinger complex. The drug is not currently approved for use in a therapeutic capacity.

See also

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References

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  • Mayer CA, Haxhiu MA, Martin RJ, Wilson CG (2006). "Adenosine A2A receptors mediate GABAergic inhibition of respiration in immature rats". J Appl Physiol. 100 (1): 91–97. doi:10.1152/japplphysiol.00459.2005. PMID 16141383.
  • Xie S, Shafer G, Wilson CG, Martin HB (2006). "In vitro adenosine detection with a diamond-based sensor". Dia Rel Mater. 15 (2–3): 225–228. Bibcode:2006DRM....15..225X. doi:10.1016/j.diamond.2005.08.018.