2-Chloroadenosine

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

Biological Activity

[Description]:

2-Chloroadenosine, a stable adenosine analogue, protects against long term development of ischaemic cell loss in the rat hippocampus. 2-Chloroadenosine is an apparent competitive inhibitor of uridine influx (apparent Ki=33 μM) and high-affinity nitrobenzylthioinosine binding (apparent Ki=0.18 mM). 2-Chloroadenosine is a transported permeant for the nucleoside transporter in human erythrocytes[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Jarvis SM,2-Chloroadenosine, a permeant for the nucleoside transporter.Biochem Pharmacol. 1985 Sep 15;34(18):3237-41.

[2]. Evans MC, et al. An adenosine analogue, 2-chloroadenosine, protects against long term development of ischaemic cell loss in the rat hippocampus.Neurosci Lett. 1987 Dec 29;83(3):287-92.

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

DownStream

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