CGS-21680 HCl

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200752

CAS#: 124431-80-7 (HCl)

Description: CGS-21680 is a specific adenosine A2A subtype receptor agonist. 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.

Chemical Structure

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CGS-21680 HCl
CAS# 124431-80-7 (HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 200752
Name: CGS-21680 HCl
CAS#: 124431-80-7 (HCl)
Chemical Formula: C23H30ClN7O6
Exact Mass: 0.00
Molecular Weight: 535.981
Elemental Analysis: C, 51.54; H, 5.64; Cl, 6.61; N, 18.29; O, 17.91

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 124431-80-7 (HCl)   120225-54-9 (free)    

Synonym: CGS21680; CGS-21680; CGS 21680; CGS-21680 HCl; CGS-21680 hydrochloride.

IUPAC/Chemical Name: 3-(4-(2-((6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanoic acid hydrochloride

InChi Key: QPHVMNOEKKJYJO-MJWSIIAUSA-N

InChi Code: InChI=1S/C23H29N7O6.ClH/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);1H/t16-,17+,18-,22+;/m0./s1

SMILES Code: O=C(O)CCC1=CC=C(CCNC2=NC(N)=C3N=CN([C@@H]4O[C@H](C(NCC)=O)[C@@H](O)[C@H]4O)C3=N2)C=C1.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:  Related: 124431-80-7 (CGS-21680 HCl) 120225-54-9 (CGS-21680 free)

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 535.98 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Jones-Cage C, Stratford TR, Wirtshafter D. Differential effects of the adenosine A(2A) agonist CGS-21680 and haloperidol on food-reinforced fixed ratio responding in the rat. Psychopharmacology (Berl). 2011 Sep 7. [Epub ahead of print] PubMed PMID: 21898173.

2: Mazzon E, Esposito E, Impellizzeri D, DI Paola R, Melani A, Bramanti P, Pedata F, Cuzzocrea S. CGS 21680, an agonist of the adenosine (A2A) receptor, reduces progression of murine type II collagen-induced arthritis. J Rheumatol. 2011 Oct;38(10):2119-29. Epub 2011 Jul 15. PubMed PMID: 21765105.

3: Impellizzeri D, Di Paola R, Esposito E, Mazzon E, Paterniti I, Melani A, Bramanti P, Pedata F, Cuzzocrea S. CGS 21680, an agonist of the adenosine (A2A) receptor, decreases acute lung inflammation. Eur J Pharmacol. 2011 Oct 1;668(1-2):305-16. Epub 2011 Jul 8. PubMed PMID: 21756897.

4: Vuaden FC, Savio LE, Bastos CM, Bogo MR, Bonan CD. Adenosine A(2A) receptor agonist (CGS-21680) prevents endotoxin-induced effects on nucleotidase activities in mouse lymphocytes. Eur J Pharmacol. 2011 Jan 25;651(1-3):212-7. Epub 2010 Nov 27. PubMed PMID: 21114987.

5: Palma AG, Muchnik S, Losavio AS. Excitatory effect of the A2A adenosine receptor agonist CGS-21680 on spontaneous and K+-evoked acetylcholine release at the mouse neuromuscular junction. Neuroscience. 2011 Jan 13;172:164-76. Epub 2010 Nov 2. PubMed PMID: 20971164.

6: Ferrante A, Martire A, Armida M, Chiodi V, Pézzola A, Potenza RL, Domenici MR, Popoli P. Influence of CGS 21680, a selective adenosine A(2A) receptor agonist, on NMDA receptor function and expression in the brain of Huntington's disease mice. Brain Res. 2010 Apr 6;1323:184-91. Epub 2010 Feb 4. PubMed PMID: 20138162.

7: Genovese T, Melani A, Esposito E, Mazzon E, Di Paola R, Bramanti P, Pedata F, Cuzzocrea S. The selective adenosine A2A receptor agonist CGS 21680 reduces JNK MAPK activation in oligodendrocytes in injured spinal cord. Shock. 2009 Dec;32(6):578-85. PubMed PMID: 19295488.

8: Font L, Mingote S, Farrar AM, Pereira M, Worden L, Stopper C, Port RG, Salamone JD. Intra-accumbens injections of the adenosine A2A agonist CGS 21680 affect effort-related choice behavior in rats. Psychopharmacology (Berl). 2008 Sep;199(4):515-26. Epub 2008 May 20. PubMed PMID: 18491078; PubMed Central PMCID: PMC2643064.

9: Mingote S, Pereira M, Farrar AM, McLaughlin PJ, Salamone JD. Systemic administration of the adenosine A(2A) agonist CGS 21680 induces sedation at doses that suppress lever pressing and food intake. Pharmacol Biochem Behav. 2008 May;89(3):345-51. Epub 2008 Jan 17. PubMed PMID: 18281083; PubMed Central PMCID: PMC2674372.

10: Selmeczy Z, Csóka B, Pacher P, Vizi ES, Haskó G. The adenosine A2A receptor agonist CGS 21680 fails to ameliorate the course of dextran sulphate-induced colitis in mice. Inflamm Res. 2007 May;56(5):204-9. PubMed PMID: 17588136; PubMed Central PMCID: PMC2225471.