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C5134

Sigma-Aldrich

2-Chloroadenosine

Synonym(s):

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

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10 MG
¥15,540
50 MG
¥40,600
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¥139,300
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¥347,200

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10 MG
¥15,540
50 MG
¥40,600
250 MG
¥139,300
1 G
¥347,200

About This Item

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

¥15,540

List Price¥22,200Save 30%

Estimated to ship onApril 05, 2025

Request a Bulk Order

form

powder

Quality Level

200

SMILES string

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

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

Gene Information

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

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Application

2-Chloroadenosine has been used:
  • as an agonist of adenosine receptors (A1R) in dorsal hippocampus (DH) and ventral hippocampus (VH) of mice[1]
  • as a component of artificial cerebrospinal fluid (aCSF) for electrophysiological experiments using hippocampal slices[2]
  • 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[3]

Biochem/physiol Actions

2-Chloroadenosine is an analog of adenosine.[4] It is an adenosine A1 receptor agonist.[5] It might possess anti-oxidant property.[6]

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

C5134-VAR:
C5134-250MG:
C5134-10MG:
C5134-5MG:
C5134-BULK:
C5134-1G:
C5134-50MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000407143
0000354060
0000337623
0000337624
0000337625

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Wen-Li Gao et al.
Bioresource technology, 118, 82-88 (2012-06-19)
2-Methyltetrahydrofuran (MeTHF), a biomass-derived compound, is a promising medium for biocatalysis and organometallic reactions. The regioselective acylation of 8-chloroadenosine (8-Cl-Ado) and its analogs was carried out in MeTHF with immobilized Penicillium expansum lipase. The lipase displayed more than twofold higher
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)
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
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
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