C141

CGS-21680 hydrochloride hydrate

Name: CGS-21680 hydrochloride hydrate
Brand: SIGMA

≥98% (HPLC), Adenosine A2A receptor agonist, solid

Synonym(s):

2-p-(2-Carboxyethyl)phenethylamino-5′-N-ethylcarboxamidoadenosine hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₂₉N₇O₆ · HCl · xH₂O

CAS Number:

124182-57-6

Molecular Weight:

535.98 (anhydrous basis)

UNSPSC Code:

12352200

PubChem Substance ID:

24277698

NACRES:

NA.77

MDL number:

MFCD11045878

Key Documents

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Product Name

CGS-21680 hydrochloride hydrate, solid

SMILES string

O.Cl.CCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)nc(NCCc4ccc(CCC(O)=O)cc4)nc23

InChI

1S/C23H29N7O6.ClH.H2O/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;1H2/t16-,17+,18-,22+;;/m0../s1

InChI key

VIRPCGAECNOLOO-VBQNEDDFSA-N

assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

DMSO: >10 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 20 mg/mL

storage temp.

−20°C

Quality Level

100

Gene Information

human ... ADORA2A(135), ADORA2B(136)

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Show Differences

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This Item	PZ0136	B2417	E8284
Sigma-Aldrich C141 CGS-21680 hydrochloride hydrate	Sigma-Aldrich PZ0136 CP-100263 dihydrochloride hydrate	Sigma-Aldrich B2417 Benzamil hydrochloride hydrate	Sigma-Aldrich E8284 (E/Z)-Endoxifen Hydrochloride Hydrate
assay ≥98% (HPLC)	assay ≥97% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form solid	form solid	form solid	form solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. room temp	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: >10 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 20 mg/mL	solubility H₂O: ≥5 mg/mL	solubility methanol: 10 mg/mL, DMSO: >20 mg/mL	solubility DMSO: >10 mg/mL
storage condition desiccated	storage condition -	storage condition desiccated	storage condition desiccated

Biochem/physiol Actions

Adenosine receptor agonist, which possesses selectivity for A₂ verses A₁ receptors.

Disclaimer

Hygroscopic

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Caffeine treatment started before injury reduces hypoxic-ischemic white-matter damage in neonatal rats by regulating phenotypic microglia polarization.

Liu Yang et al.

Pediatric research (2022-02-28)

Reducing neuroinflammatory damage is an effective strategy for treating white-matter damage (WMD) in premature infants. Caffeine can ameliorate hypoxia-ischemia-induced brain WMD; however, its neuroprotective effect and mechanism against hypoxic-ischemic WMD remain unclear. We used 3-day-old Sprague-Dawley rats to establish a

4-Pyridone-3-carboxamide-1-β-D-ribonucleoside (4PYR)-A Novel Oncometabolite Modulating Cancer-Endothelial Interactions in Breast Cancer Metastasis.

Patrycja Koszalka et al.

International journal of molecular sciences, 23(10) (2022-05-29)

The accumulation of specific metabolic intermediates is known to promote cancer progression. We analyzed the role of 4-pyridone-3-carboxamide-1-β-D-ribonucleoside (4PYR), a nucleotide metabolite that accumulates in the blood of cancer patients, using the 4T1 murine in vivo breast cancer model, and

Diminished iron concentrations increase adenosine A(2A) receptor levels in mouse striatum and cultured human neuroblastoma cells.

Seema Gulyani et al.

Experimental neurology, 215(2), 236-242 (2008-11-18)

Brain iron insufficiency has been implicated in several neurological disorders. The dopamine system is consistently altered in studies of iron deficiency in rodent models. Changes in striatal dopamine D(2) receptors are directly proportional to the degree of iron deficiency. In

[3H]CGS 21680, a selective A2 adenosine receptor agonist directly labels A2 receptors in rat brain.

M F Jarvis et al.

The Journal of pharmacology and experimental therapeutics, 251(3), 888-893 (1989-12-01)

Characterization of the adenosine A2 receptor has been limited due to the lack of available ligands which have high affinity and selectivity for this adenosine receptor subtype. In the present study, the binding of a highly A2-selective agonist radioligand, [3H]CGS

The selective adenosine A2 receptor agonist, CGS 21680, is a potent depressant of cerebral cortical neuronal activity.

J W Phillis

Brain research, 509(2), 328-330 (1990-02-19)

The A2 selective adenosine receptor agonist 2-p-(2-carboxyethyl)phenethylamino-5'-N-ethylcarboxamidoadenosine (CGS 21680) depressed the spontaneous, acetylcholine- and glutamate-evoked firing of rat cerebral sensorimotor cortical neurons. Iontophoretically applied CGS 21680 was equipotent with adenosine as a depressant and its actions were antagonized by 8-p-sulphophenyltheophylline

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