Nitrobenzylthioinosine

Names

[ Name ]:
Nitrobenzylthioinosine

[Synonym ]:
{6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine}
NBMPR
6-[(4-Nitrobenzyl)sulfanyl]-9-(β-D-ribofuranosyl)-9H-purine
S-(4-Nitrobenzyl)-6-thioinosine
EINECS 253-753-4
MFCD00005745
6-S-[(4-Nitrophenyl)methyl]-6-thioinosine
NBTI
6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine
9H-Purine, 6-[[(4-nitrophenyl)methyl]thio]-9-β-D-ribofuranosyl-

Biological Activity

[Description]:

Nitrobenzylthioinosine is an ENT1 transporter inhibitor that binds to ENT1 transporter with high affinity. Nitrobenzylthioinosine is a photoaffinity probe for adenosine uptake sites in brain. Nitrobenzylthioinosine can cross the blood-brain barrier[1][2][3].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

[Target]

ENT1 transporter[1]

[References]

[1]. Lauri Alanko, et al. Nitrobenzylthioinosine (NBMPR) binding and nucleoside transporter ENT1 mRNA expression after prolonged wakefulness and recovery sleep in the cortex and basal forebrain of rat. J Sleep Res. 2003 Dec;12(4):299-304.

[2]. C M Anderson, et al. Ability of nitrobenzylthioinosine to cross the blood-brain barrier in rats. Neurosci Lett. 1996 Nov 29;219(3):191-4.

[3]. P J Marangos, et al. [3H]nitrobenzylthioinosine is a photoaffinity probe for adenosine uptake sites in brain. Eur J Pharmacol. 1982 Dec 3;85(3-4):359-60.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
770.2±70.0 °C at 760 mmHg

[ Melting Point ]:
187-190 °C(lit.)

[ Molecular Formula ]:
C₁₇H₁₇N₅O₆S

[ Molecular Weight ]:
419.412

[ Flash Point ]:
419.6±35.7 °C

[ Exact Mass ]:
419.089966

[ PSA ]:
184.64000

[ LogP ]:
1.20

[ Appearance of Characters ]:
solid | white

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.808

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
0.1 M HCl: slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UO9025000

CHEMICAL NAME :: 9H-Purine, 6-(((4-nitrophenyl)methyl)thio)-9-beta-D-ribofuranosy l-

CAS REGISTRY NUMBER :: 38048-32-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C17-H17-N5-O6-S

MOLECULAR WEIGHT :: 419.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 8 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 43,1616,1983

Safety Information

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

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UO9025000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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Related Compounds

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