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:
Molecular Weight:
301.69
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
205-678-3
MDL number:
Beilstein/REAXYS Number:
43957
Form:
powder
Quality level:
Product Name
2-Chloroadenosine,
form
powder
Quality Level
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)
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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The effect of 2-chloroadenosine on lipid peroxide level during experimental cerebral ischemia-reperfusion in gerbils
Yavuz O, et al.
Free Radical Biology & Medicine, 22(1-2), 337-341 (1997)
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)
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