3317-61-1

Basic information

• Product Name: 5,5-DIMETHYL-1-PYRROLINE N-OXIDE
• Synonyms: DMPO;5,5-DIMETHYL-1-PYRROLINE N-OXIDE;2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE;3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE;5,5-dimethyl-1-pyrroline-1-oxide;5,5-Dimethyl-1-pyrroline N-oxide [spin trapping;spintrappingreagent;5,5-Dimethyl-1-Pyrrolidine-N-oxide
• CAS NO: 3317-61-1
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• EINECS: 222-011-1
• Product Categories: pharmacetical;Analytical Chemistry;ESR Spectrometry;Spin Trapping Reagents
• Mol File: 3317-61-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 25-29 °C(lit.)
• Boiling Point: 75 °C0.4 mm Hg(lit.)
• Flash Point: 204 °F
• Appearance: white to faintly yellow solid
• Density: 1.015 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00918mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• PKA: 2.47±0.40(Predicted)
• Stability: Stable, but light sensitive, hygroscopic and heat sensitive. Store in the dark, under an inert gas, and keep cold. Incompatible
• Merck: 14,3393
• BRN: 107603
• CAS DataBase Reference: 5,5-DIMETHYL-1-PYRROLINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)
• EPA Substance Registry System: 5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 8-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 3317-61-1(Hazardous Substances Data)

Usage

Description

Free radicals are highly reactive, short-lived species. Spin traps react with radicals, forming stable adducts that can be further studied. DMPO is a commonly-used spin trap that reacts with O-, N-, S-, and C-centered radicals. This allows their characterization when used in association with electron spin resonance and immuno-spin trapping. DMPO is water-soluble, rapidly penetrates lipid bilayers, has low toxicity, and can be used in vitro and in vivo.

Chemical Properties

white to faintly yellow solid

Uses

Different sources of media describe the Uses of 3317-61-1 differently. You can refer to the following data:
1. Spin trap agent for biological systems.
2. 5,5-Dimethyl-1-pyrroline N-oxide has been used as a spin trapping reagent to detect free radicals in electron paramagnetic resonance (EPR) based reactions.
3. 5,5-Dimethyl-1-pyrroline N-oxide is a reagent generally used either as a free-radical spin-trapping agent, or electrophilic component during the synthesis of pyrrolidine derivatives. It may also be considered as 1,3-dipole in cycloaddition processes.

Preparation

To a three-necked round bottom flask equipped with a condenser, addi-tion funnel, thermometer, and mechanical stirrer and containing 300 ml. 95% ethanol precooled to 2°C is added, all at once, 14.5 g (0.1 mole) 4-methyl-4-nitropentanol, and 13.1 g (1.2 mole) zinc dust. With rapid agita-tion, the glacial acetic acid (24.0 g, 0.4 mole) is added dropwise over a 1-hr period while maintaining the reaction temperature below 15°C. The mix-ture is stirred vigorously for 2 hr and then stored in the refrigerator for 2 days, at approximately 1°C. Then the zinc acetate is filtered and rinsed with 100 ml of ethanol. The combined ethanol factions are rotoevapo-rated to give the crude nitrone. The crude nitrone is dissolved in a 200 ml portion of dichloromethane and the latter washed two times with saturated sodium bicarbonate solution. The organic layer is dried over sodium sul-fate and the solvent rotoevaporated, to give 10.7 (94% yield) of the crude nitrone. The product was purified by double distillation (b.p. 53°C, 0.1 Torr), to give 6.8 g (60%) of the pure nitrone as a white hygroscopic solid. The H1 NMR (400 MH CDC13, Me4Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C13NMr (100 MH2, CDC13, Me4 Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).

Biological Activity

Water soluble nitric oxide spin trap; allows the measurement of oxygen-centered free radicals in biological systems at room temperature using electron spin resonance (ESR). Has a high reaction rate constant for superoxide and hydroxyl radicals, and distinguishes simultaneously among a variety of important biologically generated free radicals.

References

1) Nishizawa et al. (2004), Hydroxyl radical generation caused by the reaction of singlet oxygen with the spin trap DMPO, increases significantly in the presence of biological reductants; Mol. Pharmacol., 6 597 2) Shi et al. (2005), Evaluation of spin trapping agents and trapping conditions for detection of cell-generated reactive oxygen species; Arch. Biochem. Biophys., 437 59 3) Clement et al. (2005), Assignment of the EPR spectrum of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) superoxide spin adduct; J. Org. Chem., 70 1198 4) Gomez-Mejiba et al. (2009), Immuno-spin trapping of protein and DNA radicals: ‘tagging’ free radicals to locate and understand the redox process; Free Rad. Biol. Med., 42 530

InChI:InChI=1/C6H11NO/c1-6(2)4-3-5-7(6)8/h5H,3-4H2,1-2H3

Upstream product

• 61856-91-5 5,5-dimethyl-1-pyrroline-2-carboxylic acid 1-oxide 
• 55482-04-7 2,2-dimethyl-5-hydroperoxy-1-pyrrolidinyloxyl 
• 57620-56-1 2-(3-methyl-3-nitrobutyl)-[1,3]dioxolane 
• 57620-49-2 4-methyl-4-nitropentanal 

Downstream Products

• 3433-48-5 6,6-dimethyl-2-phenyl-hexahydro-pyrrolo[1,2-b]isoxazole 
• 71871-88-0 6,6-dimethyl-1,3,3-triphenyl-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazin-2-one 
• 7064-29-1 Decahydro-3,3-dimethyl-pyrrolo<1,2-b>-1,2-benzisoxazol-9-on 
• 7064-27-9 Hexahydro-3-acetyl-2,2,6,6-tetramethyl-pyrrolo<1,2-b>isoxazol 
• 50455-84-0 5,5-dimethyl-1-naphthalen-1-yl-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazole-2-thione 
• 7064-25-7 6.6-Dimethyl-N-t.-butyl-pyrrolo<1.2-b>isoxazol-2-carbonsaeure-amid 
• 39931-28-7 4-(5,5-dimethyl-2-thioxo-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazol-1-yl)-benzoic acid ethyl ester 
• 50455-85-1 4-(5,5-dimethyl-2-oxo-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazol-1-yl)-benzoic acid ethyl ester 
• 7064-22-4 Hexahydro-6,6-dimethyl-2-phenyl-pyrrolo<1,2-b>isoxazol-3-carbonsaeure-methylester 
• 50455-64-6 5,5-dimethyl-1-phenyl-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazole-2-thione 
• 7064-23-5 Hexahydro-6,6-dimethyl-pyrrolo<1.2-b>isoxazol-2-carbonsaeure-amid 
• 7064-18-8 Hexahydro-2,6.6-trimethyl-pyrrolo<1.2-b>isoxazol-2-carbonsaeure-methylester 
• 7064-20-2 Hexahydro-2,6.6-trimethyl-pyrrolo<1.2-b>isoxazol-2-carbonsaeure-aethylester 
• 39931-30-1 1-(4-fluoro-phenyl)-5,5-dimethyl-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazol-2-one 

Relevant articles and documents

NMR and EPR studies of the reaction of nucleophilic addition of (bi) sulfite to the nitrone spin trap DMPO

The reaction of the nitrone spin trap 5,5-dimethylpyrroline-N-oxide (DMPO) with sodium (bi)sulfite in aqueous solutions was investigated using NMR and EPR techniques. Reversible nucleophilic addition of (bi)sulfite anions to the double bond of DMPO was observed, resulting in the formation of the hydroxylamine derivative 1-hydroxy-5,5-dimethylpyrrolidine-2-sulfonic acid, with characteristic 1H and 13C NMR spectra. The reaction mechanism was suggested and corresponding equilibrium constants determined. The mild oxidation of the hydroxylamine results in the formation of an EPR-detected spectrum identical with that for the DMPO adduct with sulfur trioxide anion radical. The latter demonstrates that a non-radical addition reaction of (bi)sulfite with DMPO may contribute to the EPR detection of SO3 -? radical. This possibility must be taken into account in spin trapping analysis of sulfite radical. Copyright

COMPOSITIONS COMPRISING A NITRONE COMPOUND FOR USE IN TREATING UVEITIS

Ophthalmic pharmaceutical compositions containing a pharmaceutically acceptable ophthalmic carrier and an inflammation-treating amount of a nitrone compound are disclosed. Also disclosed are methods for treating ocular inflammation conditions, such as uveitis, using pharmaceutical compositions.

Acylation of Aldo 1-Pyrroline 1-Oxides (4,5-Dihydro-3H-pyrrole 1-Oxides) and the Oxidation of the Resulting 3-Acyloxy-1-pyrrolines (3-Acyloxy-4,5-dihydro-3H-pyrroles)

5,5-Dimethyl-1-pyrroline 1-oxide (DMPO), when treated with NaH (1 mol) followed by ethyl chloroformate, benzoyl chloride, pivaloyl chloride or 2-bromoisobutyryl bromide gave the corresponding 3-acyloxy-1-pyrrolines.With NaH (2-4 mol) followed by benzoyl chloride or 2-bromoisobutyryl bromide, DMPO gave the corresponding 2-(3'-acyloxy-1'-pyrrolin-3'-yl)-3-acyloxypyrrolidines.Acylation of the 3-phenyl and 3-methyl DMPOs also gave the corresponding 3-acyloxy-1-pyrrolines.Oxidation of the 3-acyloxy-1-pyrrolines with m-CPBA gave the correspondong oxaziridines in good yield.These oxaziridines were resistant to ring opening by acid hydrolysis, photolysis and thermolysis.