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5,5-Dimethyl-1-pyrroline N-oxide

5,5-Dimethyl-1-pyrroline N-oxide Structure
5,5-Dimethyl-1-pyrroline N-oxide structure
CAS No.
3317-61-1
Chemical Name:
5,5-Dimethyl-1-pyrroline N-oxide
Synonyms
DMPO;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;Dimethyl N;spintrappingreagent;DMPO, hydrophilic spin trap;,5-Dimethyl-1-pyrroline N-oxide;5.5-Dimethyl-1-pyroline n-oxide;5,5-Dimethyl-1-pyrroline N-oxide
CBNumber:
CB3290637
Molecular Formula:
C6H11NO
Molecular Weight:
113.16
MDL Number:
MFCD00005279
MOL File:
3317-61-1.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-09-20 08:01:04
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5,5-Dimethyl-1-pyrroline N-oxide Properties

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.
InChI 1S/C6H11NO/c1-6(2)4-3-5-7(6)8/h5H,3-4H2,1-2H3
InChIKey VCUVETGKTILCLC-UHFFFAOYSA-N
SMILES CC1(C)CCC=[N+]1[O-]
CAS DataBase Reference 3317-61-1(CAS DataBase Reference)
FDA UNII 7170JZ1QF3
UNSPSC Code 12352200
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P280-P305+P351+P338-P321
PPE Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Safety Statements  24/25
WGK Germany  3
F  8-10
HazardClass  IRRITANT
HS Code  29339900
Storage Class 10 - Combustible liquids
NFPA 704
1
0 0

5,5-Dimethyl-1-pyrroline N-oxide price More Price(73)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 92688 5,5-Dimethyl-1-pyrroline N-oxide for ESR-spectroscopy 3317-61-1 100mg $165 2026-04-30 Buy
TCI Chemical D2362 5,5-Dimethyl-1-pyrroline N-Oxide >97.0%(GC)(T) 3317-61-1 1g $128 2026-04-30 Buy
TCI Chemical D2362 5,5-Dimethyl-1-pyrroline N-Oxide >97.0%(GC)(T) 3317-61-1 5g $468 2026-04-30 Buy
Cayman Chemical 10006436 DMPO ≥98% 3317-61-1 500mg $72 2026-04-30 Buy
Cayman Chemical 10006436 DMPO ≥98% 3317-61-1 1g $137 2026-04-30 Buy
Product number Packaging Price Buy
92688 100mg $165 Buy
D2362 1g $128 Buy
D2362 5g $468 Buy
10006436 500mg $72 Buy
10006436 1g $137 Buy

5,5-Dimethyl-1-pyrroline N-oxide Chemical Properties, Uses, Production

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

Spin trap agent for biological systems.

Uses

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.

Uses

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.

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.

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

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] CHIHO NISHIZAWA. Hydroxyl radical generation caused by the reaction of singlet oxygen with a spin trap, DMPO, increases significantly in the presence of biological reductants.[J]. Free Radical Research, 2004, 38 4: 385-392. DOI:10.1080/1071576042000191772
[2] HONGLIAN SHI . Evaluation of spin trapping agents and trapping conditions for detection of cell-generated reactive oxygen species[J]. Archives of biochemistry and biophysics, 2005, 437 1: Pages 59-68. DOI:10.1016/j.abb.2005.02.028
[3] JEAN-LOUIS CLÉMENT. Assignment of the EPR Spectrum of 5,5-Dimethyl-1-pyrroline N-Oxide (DMPO) Superoxide Spin Adduct†[J]. The Journal of Organic Chemistry, 2005, 70 4: 1198-1203. DOI:10.1021/jo048518z
[4] SANDRA E. GOMEZ-MEJIBA . Immuno-spin trapping of protein and DNA radicals: “Tagging” free radicals to locate and understand the redox process[J]. Free Radical Biology and Medicine, 2009, 46 7: Pages 853-865. DOI:10.1016/j.freeradbiomed.2008.12.020

5,5-Dimethyl-1-pyrroline N-oxide synthesis

57620-49-2
3317-61-1
Synthesis of 5,5-Dimethyl-1-pyrroline N-oxide from 4-Methyl-4-nitrovaleraldehyde

5,5-Dimethyl-1-pyrroline N-oxide Preparation Products And Raw materials

Raw materials

Preparation Products

4-Methylphthalimide 99

5,5-Dimethyl-1-pyrroline N-oxide Suppliers

Global Suppliers ( 290)
Supplier Tel Email Country ProdList Advantage
Changzhou Ucheml Medicine Co., Ltd. 0519-86058959 13775231161 sales@uchemi.cn China 303 50
Anhui kuer Bioengineering Co., Ltd 0551-65171243 13856024262 kuer@kuerhuaxue.com China 2996 55
Chongqing Botao Biotechnology Co., LTD 15223382610 danny@chemdad.com China 2030 58
Puyang Borui Technology Development Co., Ltd 15203933070 450281857@qq.com China 122 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
3B Pharmachem (Wuhan) International Co.,Ltd. 18930552037 3bsc@sina.com China 15813 69
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Beijing HwrkChemical Technology Co., Ltd 89508211 18501085097 sales.bj@hwrkchemical.com China 9407 55
Energy Chemical 400-0056266 sales8178@energy-chemical.com China 44850 61
Supplier Advantage
Changzhou Ucheml Medicine Co., Ltd. 50
Anhui kuer Bioengineering Co., Ltd 55
Chongqing Botao Biotechnology Co., LTD 58
Puyang Borui Technology Development Co., Ltd 58
J & K SCIENTIFIC LTD. 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 62
3B Pharmachem (Wuhan) International Co.,Ltd. 69
TCI (Shanghai) Development Co., Ltd. 81
Beijing HwrkChemical Technology Co., Ltd 55
Energy Chemical 61

Related articles

View Latest Price from 5,5-Dimethyl-1-pyrroline N-oxide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
DMPO pictures 2026-07-15 DMPO
3317-61-1
 $39.00-83.00 99.98% 10g TargetMol Chemicals Inc.
5,5-Dimethyl-1-pyrroline N-oxide pictures 2021-07-13 5,5-Dimethyl-1-pyrroline N-oxide
3317-61-1
 $10.00-15.00 1KG 99%+ HPLC Zhuozhou Wenxi import and Export Co., Ltd
5,5-Dimethyl-1-pyrroline N-oxide pictures 2021-07-10 5,5-Dimethyl-1-pyrroline N-oxide
3317-61-1
 $10.00-15.00 1KG 99%+ HPLC Zhuozhou Wenxi import and Export Co., Ltd
  • DMPO pictures
  • DMPO
    3317-61-1
  • $39.00-83.00
  • 99.98%
  • TargetMol Chemicals Inc.

5,5-Dimethyl-1-pyrroline N-oxide Spectrum

5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)1HNMR5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)IR5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)FT-IR5,5-DIMETHYL-1-PYRROLINE N-OXIDE(3317-61-1)Raman

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2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE 3,4-Dihydro-2,2-dimethyl-2H-pyrrole N-oxide 95% 2,2-Dimethyl-3,4-Dihydro-2H-Pyrrole 1-Ox 5,5-dimethyl-1-pyrroline-1-oxide 5,5-Dimethyl-1-pyrroline N-oxide [spin trapping spintrappingreagent 1-Oxylato-2,2-dimethyl-3,4-dihydro-2H-pyrrole-1-ium 3,4-Dihydro-1-oxylato-2,2-dimethyl-2H-pyrrolium 5,5-Dimethyl-1-Pyrrolidine-N-oxide 5,5-DIMETHYL-1-PYRROLINE N-OXIDE, [SPIN TRAPPING REAGENT] 5,5-DIMETHYL-1-PYRROLINE N-OXIDE [SPIN TRAPPING REAGENT] 97+% 5,5-DIMETHYL-1-PYRROLINE N-OXIDE 99% 2,2-dimethyl-1-oxidanidyl-3,4-dihydropyrrol-1-ium 2,2-dimethyl-1-oxido-1-pyrrolin-1-ium 2,2-dimethyl-1-oxido-3,4-dihydropyrrol-1-ium 5,5-Dimethyl-1-pyrroline N-oxide ,97% 5,5-Dimethyl-1-pyrroline N-oxide,DMPO 2,2-diMethyl-2,3-dihydro-1H-pyrrole 1-oxide 5,5-Dimethyl-1-pyrrolineN-Oxide> Dimethyl N ,5-Dimethyl-1-pyrroline N-oxide 5,5-Dimethyl-1-pyrroline N-Oxide, ≥ 97.0% DMPO, hydrophilic spin trap 2-Dimethyl-3,4-dihydro-2H-pyrrole1-oxide 5,5-Dimethyl-1-pyrroline N-oxide 5.5-Dimethyl-1-pyroline n-oxide 3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE DMPO 5,5-Dimethyl-1-pyrroline N-oxide 3317-61-1 Enzymes, Inhibitors, and Substrates Pyrrolines Nitric Oxide Metabolism Nitric Oxide Scavengers ESR Spectrometry Spin Trapping Reagents Building Blocks Biochemicals and Reagents Application Index BioChemical Cell Signaling Enzymes Heterocyclic Building Blocks pharmacetical Analytical Chemistry ESR Spectrometry Spin Trapping Reagents