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57470 Sigma-Aldrich

Inosine

crystallized, ≥99.0% (HPLC)

Synonym: (−)-Inosine, Hypoxanthine 9-β-D-ribofuranoside

  • CAS Number 58-63-9

  • Empirical Formula (Hill Notation) C10H12N4O5

  • Molecular Weight 268.23

  •  Beilstein/REAXYS Number 624896

  •  EC Number 200-390-4

  •  MDL number MFCD00066770

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Properties

assay   ≥99.0% (HPLC)
optical activity   [α]20/D −76±2°, c = 1% in 0.1 M NaOH
quality   crystallized
ign. residue   ≤0.05%
mp   222-226 °C (dec.) (lit.)
solubility   H2O: soluble 50 mg/mL, clear, colorless
SMILES string   OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3C(=O)NC=Nc23
InChI   1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
InChI key   UGQMRVRMYYASKQ-KQYNXXCUSA-N

Description

Application

Inosine was used in a study to understand the protective effect of adenosine that is mediated by inosine in rat astrocyte cultures subjected to combined glucose-oxygen deprivation. It was used as a supplement in a medium to obtain fully differentiated human colonic surface-like cells in a study. The product was used to study the effects of inosine on left ventricular contractile force, circumflex blood flow, heart rate, and arterial pressure in mongrel dogs. It was used to study the anti-inflammatory effects of inosine in human monocytes, neutrophils and epithelial cells in vitro.

Biochem/physiol Actions

Inosine is a potent stimulator of nerve growth factor (NGF) induced neurite outgrowth. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing.

Inosine is an endogenous purine nucleoside, which is formed during the breakdown of adenosine by adenosine deaminase. Upon metabolic stress or from the sympathetic nervous system, inosine is released into the extracellular space from cells. In murine experimental system, inosine is shown to exert immunomodulatory, anti-inflammatory and anti-shock effects.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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I4125 Inosine, ≥99% (HPLC)

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