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Merck
CN

C5134

2-Chloroadenosine

adenosine A1 receptor agonist, powder

Synonym(s):

2-CADO, 6-Amino-2-chloropurine riboside

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About This Item

Empirical Formula (Hill Notation):
C10H12ClN5O4
CAS Number:
146-77-0
Molecular Weight:
301.69
NACRES:
NA.77
PubChem Substance ID:
24277688
UNSPSC Code:
12352200
EC Number:
205-678-3
MDL number:
MFCD00005734
Beilstein/REAXYS Number:
43957

Key Documents

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Product Name

2-Chloroadenosine,

InChI

1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

InChI key

BIXYYZIIJIXVFW-UUOKFMHZSA-N

SMILES string

Nc1nc(Cl)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

form

powder

Quality Level

200

Gene Information

human ... ADORA1(134), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Related Categories

Application

2-Chloroadenosine has been used:
  • as an agonist of adenosine receptors (A1R) in dorsal hippocampus (DH) and ventral hippocampus (VH) of mice
  • as a component of artificial cerebrospinal fluid (aCSF) for electrophysiological experiments using hippocampal slices
  • as an internal standard in solid phase extraction coupled with liquid chromatography-tandem mass spectrometry (XLC-MS/MS) for the quantification of certain metabolites from axonal lysates and dorsal root ganglia (DRG) neurons

Biochem/physiol Actions

2-Chloroadenosine is an analog of adenosine. It is an adenosine A1 receptor agonist. It might possess anti-oxidant property.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000507535
0000507534
0000507534
0000507535
0000407143

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Sheila Weitzman et al.
Pediatric blood & cancer, 53(7), 1271-1276 (2009-09-05)
A prospective phase II Histiocyte Society study, LCH-S-98, evaluated the efficacy of 2-chlorodeoxyadenosine (2-CdA) monotherapy as salvage therapy in Langerhans cell histiocytosis (LCH). Patients with poor and intermediate risk LCH not responsive to initial therapy and patients with low-risk chronic
Effect of locally infused 2-chloroadenosine, an A1 receptor agonist, on spontaneous and evoked dopamine release in rat neostriatum
Ballarin M, et al.
Neuroscience Letters, 185(1), 29-32 (1995)
2-Chloroadenosine decreases long-term potentiation in the hippocampal CA1 area of the rat
de Mendoncca A and Ribeiro J A
Neuroscience Letters, 118(1), 107-111 (1990)
Javier Díaz-Alonso et al.
eLife, 9 (2020-08-25)
We tested the proposal that the C-terminal domain (CTD) of the AMPAR subunit GluA1 is required for LTP. We found that a knock-in mouse lacking the CTD of GluA1 expresses normal LTP and spatial memory, assayed by the Morris water
Menglong Zeng et al.
Neuron, 104(3), 529-543 (2019-09-08)
Transmembrane AMPA receptor (AMPAR) regulatory proteins (TARPs) modulate AMPAR synaptic trafficking and transmission via disc-large (DLG) subfamily of membrane-associated guanylate kinases (MAGUKs). Despite extensive studies, the molecular mechanism governing specific TARP/MAGUK interaction remains elusive. Using stargazin and PSD-95 as the
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