5,5-DIMETHYL-1-PYRROLINE N-OXIDE

Synonym(s):DMPO

CAS NO.：3317-61-1
Empirical Formula: C6H11NO
Molecular Weight: 113.16
MDL number: MFCD00005279
EINECS: 222-011-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-06 18:33:45

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Structural

What is 5,5-DIMETHYL-1-PYRROLINE N-OXIDE?

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

The Uses of 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

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.

The Uses of 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

Spin trap agent for biological systems.

The Uses of 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

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.

What are the applications of Application

DMPO is a cell permeable hydrophillic spin trap agent for superoxide detection

Preparation

To a three-necked round bottom flask equipped with a condenser, addition 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 agitation, 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 mixture 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 sulfate 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).
Preparation of 5,5-dimethyl-l-pyrroline-N-oxide

Definition

ChEBI: 5,5-dimethyl-1-pyrroline N-oxide is a member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation. It has a role as a neuroprotective agent and a spin trapping reagent. It is functionally related to a 5,5-dimethyl-1-pyrroline.

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.

Physiological effects

5,5-dimethyl-1-pyrroline N-oxide is used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation. It has a role as a neuroprotective agent and a spin trapping reagent.

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

Properties of 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

Melting point:	25-29 °C (lit.)
Boiling point:	75 °C/0.4 mmHg (lit.)
Density	1.015 g/mL at 25 °C (lit.)
refractive index	n20/D 1.496(lit.)
Flash point:	204 °F
storage temp.	-20°C
solubility	Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
form	Pale yellow solid or oil.
pka	2.47±0.40(Predicted)
color	Pale yellow
Merck	14,3393
BRN	107603
Stability:	Stable, but light sensitive, hygroscopic and heat sensitive. Store in the dark, under an inert gas, and keep cold. Incompatible with strong oxidizing agents, moisture.
CAS DataBase Reference	3317-61-1(CAS DataBase Reference)

Safety information for 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P321:Specific treatment (see … on this label). P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.