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2-Chloroadenosine

2-Chloroadenosine Structure
2-Chloroadenosine structure
CAS No.
146-77-0
Chemical Name:
2-Chloroadenosine
Synonyms
(2R,3R,4S,5R)-2-(6-aMino-2-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;CHLOROADENOSINE;CADO;Cl AS;Cl-Ado;2-CADO;CI-ADO;AT-265B;2-Cl-Ar;2-CL-ADO
CBNumber:
CB5398979
Molecular Formula:
C10H12ClN5O4
Molecular Weight:
301.69
MDL Number:
MFCD00005734
MOL File:
146-77-0.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-09-10 08:17:50
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2-Chloroadenosine Properties

Melting point 162 °C
Boiling point 591.8±60.0 °C(Predicted)
Density 1.8359 (rough estimate)
refractive index -50 ° (C=0.1, H2O)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility H2O: 10 mg/mL, clear, colorless
pka 13.05±0.70(Predicted)
form Solid
color White to Off-White
Water Solubility Soluble in water.
BRN 43957
InChI 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
InChIKey BIXYYZIIJIXVFW-UUOKFMHZSA-N
SMILES OC[C@H]1O[C@@H](N2C3C(=C(N=C(Cl)N=3)N)N=C2)[C@H](O)[C@@H]1O
CAS DataBase Reference 146-77-0(CAS DataBase Reference)
FDA UNII 7W7ZUG45G8
NIST Chemistry Reference Adenosine, 2-chloro-(146-77-0)
UNSPSC Code 12352200
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338
PPE Eyeshields, Gloves, type N95 (US)
Safety Statements  24/25
WGK Germany  3
RTECS  AU7357550
HS Code  29349990
Storage Class 11 - Combustible Solids
Toxicity LD50 oral in mouse: > 100mg/kg
NFPA 704
0
3 0

2-Chloroadenosine price More Price(92)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C5134 2-Chloroadenosine 146-77-0 10mg $117 2026-04-30 Buy
Sigma-Aldrich C5134 2-Chloroadenosine 146-77-0 1g $3240 2026-04-30 Buy
TCI Chemical C2192 2-Chloroadenosine Hydrate >98.0%(HPLC)(T) 146-77-0 1g $109 2026-04-30 Buy
TCI Chemical C2192 2-Chloroadenosine Hydrate >98.0%(HPLC)(T) 146-77-0 100mg $17 2026-04-30 Buy
Cayman Chemical 15612 2-Chloroadenosine ≥98% 146-77-0 10mg $36 2026-04-30 Buy
Product number Packaging Price Buy
C5134 10mg $117 Buy
C5134 1g $3240 Buy
C2192 1g $109 Buy
C2192 100mg $17 Buy
15612 10mg $36 Buy

2-Chloroadenosine Chemical Properties,Uses,Production

Uses

2-Chloroadenosine is an adenosine analogue that is not hydrolyzed by adenosine deaminase. 2-Chloroadenosine increases the rate of dopa production in intact pheochromocytoma cells, it increases the content of cAMP in the cells, and it causes a stable activation of tyrosine hydroxylase, as measured in vitro. The action of 2-Chloroadenosine is not dependent upon extracellular Ca2+. In other experiments, we have found that 2-chloroadenosine increases the activity of adenylate cyclase in membrane fractions prepared from the pheochromocytoma. These data provide support for the hypothesis that 2-Chloroadenosine causes a cAMP-mediated phosphorylation of tyrosine hydroxylase in pheochromocytoma cells. Chromaffin cells and adrenergic neurons store and release adenine nuc1eotides together with catecho1amines. The adenosine formed by the hydrolysis of these nucleotides may be involved in the. physiological regulation of adenylate cyclase activity and of tyrosine hydroxylase activity. To date , however, we have no evidence for such a role of adenosine in normal chromaffin cells or in adrenergic neurons.

Chemical Properties

White to Off-White Crystalline Sold

Uses

A selective A1-adenosine receptor agonist. Induces apoptosis

Uses

Selective A1 adenosine receptor agonist. Since 2-chloroadenosine is not deaminated by adenosine deaminase and is less rapidly taken up by the brain than adenosine, 2-chloroadenosine led to more marked increase in CBF than adenosine.

Uses

2-Chloroadenosine is used as a selective A1-adenosine receptor agonist, and also Induces apoptosis.

Definition

A metabolically stable analog of adenosine which acts as an adenosine receptor agonist. The compound has a potent effect on the peripheral and central nervous system.

Biological Activity

Metabolically stable analog of adenosine that behaves as an adenosine receptor agonist (K i values are 300, 80 and 1900 nM for A 1 , A 2A and A 3 receptors respectively). Anticonvulsive in vivo .

Biochem/physiol Actions

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

Pharmacology

2-chloroadenosine (2-CAdo) is an adenosine deaminase-resistant analogue of adenosine, widely used as an adenosine receptor agonist. This compound has been shown to induce apoptosis in several cell types either via activation of adenosine receptors or via intracellular metabolism. However, the molecular mechanisms of 2-CAdo-induced apoptosis are unclear. Here, we analyzed the effects of 2-CAdo in the leukemia cell line EHEB. 2-CAdo was found to induce apoptosis in EHEB cells, as shown by caspase-3 activation, DNA fragmentation, poly(ADP-ribose) polymerase (PARP) cleavage and phosphatidylserine exposure. Cytotoxicity of 2-CAdo was completely suppressed by 5-iodotubercidin, an adenosine kinase inhibitor, indicating that apoptosis induced by 2-CAdo was the result of its intracellular metabolism. Accordingly, we found that 2-CAdo was efficiently converted into 2-chloroATP. In parallel, a decrease of intracellular ATP concentration as well as a general inhibition of macromolecular synthesis, involving DNA, RNA and protein synthesis, was observed. Moreover, 2-CAdo induced cytochrome c release into the cytosol, indicating activation of the intrinsic pathway of apoptosis. This was found associated with a decline in Mcl-1 protein level and p53-independent. Inhibition of AMP deaminase by coformycin markedly prevented ATP depletion, and also significantly reduced 2-CAdo cytotoxicity and caspase-3 activation. In conclusion, our data show that intracellular metabolism of 2-CAdo can lead to activation of the intrinsic pathway of apoptosis and that ATP depletion, in addition to the accumulation of the triphosphate analogue, contributes to 2-CAdo-induced apoptosis.

storage

Store at +4°C

Purification Methods

Purify 2-chloroadenosine by recrystallisation from H2O (~1% in cold), and it has max at 264 nm (pH 1 and 7) and 265 nm (pH 13) in H2O. [Brown & Weliky J Org Chem 23 125 1958, Schaeffer & Thomas J Am Chem Soc 80 3738 1958, IR: Davoll & Lewy J Am Chem Soc 74 1563 1952, Beilstein 26 III/IV 3725.]

2-Chloroadenosine synthesis

1839-18-5
58-96-8
146-77-0
Synthesis of 2-Chloroadenosine from 2-Chloroadenine and Uridine

2-Chloroadenosine Preparation Products And Raw materials

Raw materials

Preparation Products

2-Azidoadenosine 2-Chloro-2',3',5'-tris-O-[(1,1-diMethylethyl)diMethylsilyl]-adenosine

2-Chloroadenosine Suppliers

Global( 503)Suppliers
Supplier Tel Email Country ProdList Advantage
Nanjing Redwood Fine Chemical Co., Ltd. 158-05183379 15805183379 zjp@redwood.com.cn China 255 60
Shanghai Boyle Chemical Co., Ltd. 021-50182298 021-50180596 sales@boylechem.com China 2202 55
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
INTATRADE GmbH +49 3493/605464 sales@intatrade.de Germany 3563 66
3B Pharmachem (Wuhan) International Co.,Ltd. 18930552037 3bsc@sina.com China 15813 69
TAIYUAN RHF CO.,LTD. +86 351 7031519 sales@RHFChem.com China 2334 56
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Beijing HwrkChemical Technology Co., Ltd 89508211 18501085097 sales.bj@hwrkchemical.com China 9407 55
Energy Chemical 400-0056266 sales8178@energy-chemical.com China 44850 61
Supplier Advantage
Nanjing Redwood Fine Chemical Co., Ltd. 60
Shanghai Boyle Chemical Co., Ltd. 55
J & K SCIENTIFIC LTD. 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 62
INTATRADE GmbH 66
3B Pharmachem (Wuhan) International Co.,Ltd. 69
TAIYUAN RHF CO.,LTD. 56
TCI (Shanghai) Development Co., Ltd. 81
Beijing HwrkChemical Technology Co., Ltd 55
Energy Chemical 61

View Lastest Price from 2-Chloroadenosine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Chloroadenosine pictures 2026-09-11 2-Chloroadenosine
146-77-0
 1KG 98%min HPLC 100KGS WUHAN FORTUNA CHEMICAL CO., LTD
2-Chloroadenosine pictures 2026-09-10 2-Chloroadenosine
146-77-0
 $64.00-133.00 99.24% 10g TargetMol Chemicals Inc.
2-chloroadenosine pictures 2026-09-04 2-chloroadenosine
146-77-0
 1Kg 98% 20Ton Xinxiang Aurora Biotechnology Co.,Ltd.

2-Chloroadenosine Spectrum

2-Chloroadenosine(146-77-0)1HNMR2-Chloroadenosine(146-77-0)IR12-Chloroadenosine(146-77-0)IR2

146-77-0(2-Chloroadenosine)Related Search:

2-Amino-6-chloropurine Riboside Adenine Purine 2-Chloropurine 8-Chloroadenosine
6-AMINO-2-CHLOROPURINE RIBOSIDE HEMIHYDRATE,2-CHLOROADENOSINE HEMIDYDRATE,2-CHLOROADENOSINE HEMIHYDRATE 6-Chloropurine riboside Cladribine 2-Chloroadenosine 5'-Chloro-5'-deoxyadenosine
8-Chloro-cAMP 8-Chloroadenosine-3',5'-cyclic monophosphorothioate, RP-isomer sodium salt ascamycin DIINOSINE PENTAPHOSPHATE 2-Chloroadenosine 5’-Monophosphate
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1of4

2-CADO 6-Amino-2-chloropurine Riboside 6-Amino-2-chloro-9-(beta-D-ribofuranosyl)purine (2R,3R,4S,5R)-2-(6-aMino-2-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)oxolane-3,4-diol 2-Chloroadenosine≥ 98% (HPLC) 2-chloro-adenosin Cl AS Cl-Ado 2-chloropurine riboside 6-AMINO-2-CHLOROPURINE RIBOSIDE 2-CL-ADO 2-CHLOROADENOSINE 2-CHLORO-D-ADENOSINE 2-CADO CHLOROADENOSINE Regadenoson Impurity 5 2-Cl-Ado / 2-CADO 2-CADO,6-Amino-2-chloropurine riboside 6-Amino-2-chloropurine Ribosid 6-amino-2-chloro-9-(beta-d-ribofuranosyl)purine 2-Chloroadenosine Hydrate 2-CHLOROADENOSINE (6-AMINO-2-CHLOROPURINE RIBOSIDE) 9-[3α,4α-Dihydroxy-5β-(hydroxymethyl)tetrahydrofuran-2β-yl]-2-chloro-9H-purine-6-amine Antibiotic AT-265B AT-265B CI-ADO CADO 6-Amino-2-chloropuri NSC 36896 2-chloroadenine nucleoside 2-Chloroadenosine Hydrate> Adenosine, 2-chloro- 2-Chloroadenosine USP/EP/BP 2-Cl-Ar 2-Chloroadenosine,ADA inhibitor,antimalarial agent, metabolite of cladribine GL100647 Nicotinamide nucleoside impurities (3R, 4S, 5R)-2-(6-amino-2-chloro-9H-purin-9yl)-5-(hydroxymethyl) tetrahydrofuran-3, 4-diol 2-Chloroadenosine,98% 2-Chloroadenosine (CADO), Adenosine agonist 2-Chloroadenosine, 10 mM in DMSO (2R,3R,4S,5R)-2-(6-aMino-2-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol 146-77-0 147-77-0 C10H12ClN5O4xH2O C10H12ClN5O4 Nucleosides, Nucleotides, Oligonucleotides Nucleoside Analogs Biochemicals and Reagents BioChemical Adenosine Adenosine receptor 13C & 2H Sugars Miscellaneous Biochemicals Bases & Related Reagents Carbohydrates & Derivatives Heterocycles Nucleotides Biochemistry Nucleosides and their analogs Nucleosides, Nucleotides & Related Reagents