CGS-21680

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{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 403602802

| ImageFile = CGS21680.png

| IUPACName = 3-[4-(2-{[6-Amino-9-(N-ethyl-β-D-ribofuranosyluronamide)-9H-purin-2-yl]amino}ethyl)phenyl]propanoic acid

| SystematicName = 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

| OtherNames = CGS 21680

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 120225-54-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T5HB1E831H

| PubChem = 3086599

| IUPHAR_ligand2 = 424

| IUPHAR_ligand = 375

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 73283

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 331372

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 2343185

| SMILES = O=C(O)CCc1ccc(cc1)CCNc2nc(c3ncn(c3n2)[C@@H]4O[C@H](C(=O)NCC)[C@@H](O)[C@H]4O)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

| InChIKey = PAOANWZGLPPROA-RQXXJAGIBL

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = PAOANWZGLPPROA-RQXXJAGISA-N

}}

|Section2={{Chembox Properties

| Formula = C23H29N7O6

| MolarMass = 499.52

| Appearance =

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|Section3={{Chembox Hazards

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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

References

  • {{cite journal |vauthors=Mayer CA, Haxhiu MA, Martin RJ, Wilson CG |title=Adenosine A2A receptors mediate GABAergic inhibition of respiration in immature rats |journal=J Appl Physiol |volume=100 |issue=1 |pages=91–97 |year=2006 |pmid=16141383 |doi=10.1152/japplphysiol.00459.2005}}
  • {{cite journal |vauthors=Xie S, Shafer G, Wilson CG, Martin HB |title=In vitro adenosine detection with a diamond-based sensor |journal=Dia Rel Mater |volume=15 |issue=2–3 |pages=225–228 |year=2006 |doi=10.1016/j.diamond.2005.08.018 |bibcode=2006DRM....15..225X }}

{{Adenosinergics}}

Category:Nucleosides

Category:Purines

Category:Carboxamides

Category:Adenosine receptor agonists

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