3393. DMPO

Nomenclature

CAS number: 3317-61-1
3,4-Dihydro-2,2-dimethyl-2H-pyrrole 1-oxide; 5,5-dimethyl-1-pyrroline 1-oxide.
C6H11NO; mol wt 113.16.
C 63.68%, H 9.80%, N 12.38%, O 14.14%.

Description and references

Nitrone spin trap. Prepn: R. Bonnett et al., J. Chem. Soc. 1959, 2094; D. L. Haire et al., J. Org. Chem. 51, 4298 (1986); and purification: E. G. Janzen et al., Chem. Biol. Interact. 70, 167 (1989). uv absorption: L. S. Kaminsky, M. Lamchen, J. Chem. Soc. 1968, 1085. Use as spin trap in biological systems: A. I. Cederbaum, G. Cohen, Arch. Biochem. Biophys. 204, 397 (1980); A. S. W. Li et al., Biochem. Biophys. Res. Commun. 146, 1191 (1987); for neutrophil activation studies: B. E. Britigan, D. R. Hamill, Arch. Biochem. Biophys. 275, 72 (1989); eidem, Free Radical Biol. Med. 8, 459 (1990); in reperfusion injury: C. M. Arroyo et al., FEBS Lett. 221, 101 (1987); A. Tosaki, P. Braquet, Am. Heart J. 120, 819 (1990). Use in HPLC quantitation of oxygen free radicals in vivo: P. S. Rao et al., Chromatographia 30, 19 (1990).

Chemical structure

Properties

Nitrone as white crystalline solid. Very hygroscopic. Turns yellow with time even at -20°C sealed under vacuum and protected from light. uv max in cyclohexane: 246 nm (ε 9000); ethanol: 234 nm (ε 7700); water: 226 nm (ε 8600); N-hydrochloric acid: 226 nm (ε 7000); ether: 246 nm.

Use

Spin trap agent for biological systems.