2-Chloroadenosine

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Names

[ CAS No. ]:
146-77-0

[ Name ]:
2-Chloroadenosine

[Synonym ]:
6-Amino-2-chloro-9-(β-D-ribofuranosyl)purine Hydrate
2-CADO,6-Amino-2-chloropurine riboside
2-Chloroadenosine
6-Amino-2-chloropurine Riboside Hydrate
2-CADO Hydrate
EINECS 205-678-3
(2R,3R,4S,5R)-2-(6-Amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol
MFCD00005734
Adenosine, 2-chloro-
2-Chlor-9-(β-D-ribofuranosyl)-9H-purin-6-amin
6-Amino-2-Chloropurine Riboside
2-chloro adenosine

Chemical & Physical Properties

[ Density]:
2.2±0.1 g/cm3

[ Boiling Point ]:
643.3±65.0 °C at 760 mmHg

[ Melting Point ]:
162 °C

[ Molecular Formula ]:
C10H12ClN5O4

[ Molecular Weight ]:
301.686

[ Flash Point ]:
342.8±34.3 °C

[ Exact Mass ]:
301.057770

[ PSA ]:
139.54000

[ LogP ]:
-0.46

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.912

[ Water Solubility ]:
H2O: 10 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU7357550
CHEMICAL NAME :
Adenosine, 2-chloro-
CAS REGISTRY NUMBER :
146-77-0
BEILSTEIN REFERENCE NO. :
0043957
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C10-H12-Cl-N5-O4
MOLECULAR WEIGHT :
301.72
WISWESSER LINE NOTATION :
T56 BN DN FN HNJ GG IZ D- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 118,95,1959
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 118,95,1959 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
603 ug/kg
SEX/DURATION :
female 11-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 25(2),35A,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AU7357550

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 9-[2,3,5-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL]-2,6-DICHLOROPURINE
  • 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride
  • Inosine,2-chloro-6-O-methyl- (9CI)
  • 2',3',5'-Tri-O-acetyl-2-aMino-6-chloropurine Riboside
  • Guanosine
  • 2',3',5'-Triacetylguanosine
  • b-D-Ribofuranose 1-acetate 2,3,5-tribenzoate

DownStream

  • Cladribine
  • 2-THIOADENOSINE
  • 2-Azidoadenosine
  • 2-Chloro-2',3',5'-tris-O-[(1,1-dimethylethyl)dimethylsilyl]-adenosine
  • Adenosine
  • 2-(4-BROMO-THIOPHEN-2-YL)-ETHYLAMINE
  • 2-[2-(4-bromo-2-thienyl)-ethylamino]-adenosine
  • Adenosine,2-chloro-2',3'-O-(1-methylethylidene)- (9CI)
  • Guanosine
  • 2-Methylaminoadenosine

Articles

Hypoxanthine uptake by skeletal muscle microvascular endothelial cells from equilibrative nucleoside transporter 1 (ENT1)-null mice: effect of oxidative stress.

Microvasc. Res. 98 , 16-22, (2015)

Adenosine is an endogenous regulator of vascular tone. This activity of adenosine is terminated by its uptake and metabolism by microvascular endothelial cells (MVEC). The predominant transporter invo...

Oxidative stress modulates nucleobase transport in microvascular endothelial cells

Microvasc. Res. 95 , 68-75, (2014)

Purine nucleosides and nucleobases play key roles in the physiological response to vascular ischemia/reperfusion events. The intra- and extracellular concentrations of these compounds are controlled, ...

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...


More Articles

Related Compounds

  • 2-chloroadenosine
  • 2-chloroadenosine tipds
  • 2-chloroadenosine hydrate
  • 3'-Deoxy-2-chloroadenosine
  • 2-Chloroadenosine hemidydrate
  • β-L-2'-deoxy-2-chloroadenosine
  • Methyl 2-amino-2-[1-(5-methylpyridin-2-yl)cyclopropyl]acetate
  • Methyl 2-hydroxy-3,3-dimethyl-4-(1-methylpyrrolidin-2-yl)butanoate
  • 6-(1-bromo-2-methylpropan-2-yl)-3H-[1,2,3]triazolo[4,5-b]pyridine
  • Methyl 3-(1-bromo-2-methylpropan-2-yl)benzoate
  • 4-(2-bromopropyl)-3-(4-fluorophenyl)-1H-pyrazole
  • 4-(2-Chloro-6-nitrophenyl)pyrrolidin-2-one
  • 2,2-Difluoro-3-(3-methyl-2-nitrophenyl)propan-1-amine
  • 5-(1-bromo-2-methylpropan-2-yl)-1,4-dimethyl-1H-pyrazole
  • tert-butyl N-{2-[(1R)-2-amino-1-hydroxyethyl]-4-chlorophenyl}carbamate
  • {[5-(3-Bromoprop-1-en-2-yl)-2-methoxyphenyl]methyl}dimethylamine
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