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C141

Sigma-Aldrich

CGS-21680 hydrochloride hydrate

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)
MDL number:
MFCD11045878
UNSPSC Code:
12352200
PubChem Substance ID:
24277698
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

100

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

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

Gene Information

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

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Biochem/physiol Actions

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

Caution

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
N Levens et al.
The Journal of pharmacology and experimental therapeutics, 257(3), 1005-1012 (1991-06-01)
This study compares the renal actions of the A2 selective adenosine agonist, CGS 21680A, with the A1 selective adenosine agonist, N6-cyclopentyladenosine (CPA), and the nonselective agonist, 5'-N-ethylcarboxamide adenosine (NECA), in the anesthetized dog. Initial receptor binding studies in dog brain
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
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