Compounds > 1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine
Page last updated: 2024-12-07

1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine, also known as **TEMPOL**, is a **stable nitroxide radical**. This means it has an unpaired electron, making it highly reactive and useful for various applications in research, particularly in biological and chemical fields.

**Why is TEMPOL important for research?**

* **Antioxidant properties:** TEMPOL can scavenge reactive oxygen species (ROS), like superoxide radicals and hydroxyl radicals, which are implicated in oxidative stress and damage to cells. This makes TEMPOL a promising therapeutic agent for diseases associated with oxidative stress, such as neurodegenerative diseases, heart disease, and cancer.
* **Spin trapping:** TEMPOL can trap free radicals and form a stable adduct, which can be detected using electron paramagnetic resonance (EPR) spectroscopy. This allows researchers to study the production and kinetics of free radicals in biological systems.
* **Biological signaling:** TEMPOL has been shown to modulate various signaling pathways involved in inflammation, cell proliferation, and apoptosis. This makes it a valuable tool for understanding and potentially manipulating these processes.
* **Drug delivery:** TEMPOL can be conjugated to drugs to improve their delivery and efficacy. Its small size and ability to cross cell membranes allows it to potentially target specific tissues and cells.
* **Imaging agent:** TEMPOL's paramagnetic properties make it useful as a contrast agent for magnetic resonance imaging (MRI). This allows for non-invasive visualization of biological processes and tissue changes.

**Research applications:**

* **Neuroprotection:** TEMPOL has been investigated for its potential neuroprotective effects in conditions like Parkinson's disease and Alzheimer's disease.
* **Cardiovascular disease:** TEMPOL has shown potential to reduce inflammation and oxidative stress in the cardiovascular system, potentially mitigating the risk of heart disease.
* **Cancer therapy:** TEMPOL is being studied for its ability to sensitize cancer cells to chemotherapy and radiation, potentially improving treatment outcomes.
* **Diabetes:** TEMPOL has been investigated for its ability to improve insulin sensitivity and reduce oxidative stress in diabetic patients.

**Overall, TEMPOL is a versatile molecule with a wide range of applications in research and potentially in clinical medicine. Its antioxidant, spin-trapping, signaling, and drug delivery properties make it a valuable tool for understanding and manipulating biological processes.**

Cross-References

ID SourceID
PubMed CID98642
CHEMBL ID326931
SCHEMBL ID85990
MeSH IDM0271017

Synonyms (42)

Synonym
1-hydroxy-2,2,6,6-tetramethyl-4-piperidinone
4-piperidinone, 1-hydroxy-2,2,6,6-tetramethyl-
3637-11-4
mls003106434 ,
nsc-156571
nsc156571
smr001821337
CHEMBL326931
1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one
WSGDRFHJFJRSFY-UHFFFAOYSA-N
tempone-h
nsc 156571
1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine
FT-0619336
FT-0607918
AKOS015904833
SCHEMBL85990
1oxyl-2,2,6,6-tetramethyl-4-piperidone
1-oxyl-2,2,6,6-tetramethylpiperidin-4-one
1-oxyl-4-oxo-2,2,6,6-tetramethylpiperidine
1-oxyl-2,2,6,6-tetramethyl-4-piperidone
1-oxyl-2,2,6,6-tetramethyl-piperidin-4-one
1-oxyl-2,2,6,6-tetramethylpiperid-4-one
1-oxyl-2,2,6,6-tetramethylpiperidin -4-one
n-hydroxy-2,2,6,6-tetramethylpiperidin-4-one
J-200075
(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl)oxidanyl
DTXSID30189892
GEO-02074
4-oxo-2,2,6,6-tetramethylpiperidinoxy
H10884
2,2,6,6-tetramethyl-4-piperidone 1-oxyl
FS-4090
1-hydroxy-2,2,6,6-tetramethyl-4-oxo-piperidine
Q27268928
1-lambda1-oxidanyl-2,2,6,6-tetramethyl(115n)azinan-4-one
GS-0688
STARBLD0001853
HY-23033
oxo-2,2,6,6-tetramethylpiperidinooxy
1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-one
O0521
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID216900Mean surviving fraction of V79 cells following a 12-Gy dose of radiation.1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Studies of structure-activity relationship of nitroxide free radicals and their precursors as modifiers against oxidative damage.
AID216891Mean surviving fraction of V79 cells following a 1-h exposure to H2O21998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Studies of structure-activity relationship of nitroxide free radicals and their precursors as modifiers against oxidative damage.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (40.00)18.2507
2000's3 (30.00)29.6817
2010's2 (20.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.92

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.92 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
salicylic acid
Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).		2.0210monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		1.9910sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.0410elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		2.420monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
5,5-dimethyl-1-pyrroline-1-oxide
5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : 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.		1.99101-pyrroline nitronesneuroprotective agent;
spin trapping reagent
2,2'-azobis(2-amidinopropane)
2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator		1.9910monoazo compound
molsidomine
Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.		2.4120ethyl ester;
morpholines;
oxadiazole;
zwitterion		antioxidant;
apoptosis inhibitor;
cardioprotective agent;
nitric oxide donor;
vasodilator agent
linsidomine
linsidomine: RN given refers to parent cpd; structure		2.4120morpholines
tempol-h
TEMPOL-H: hydroxylamine (protonated, reduced) form of TEMPOL; a N-hydroxyl form of LASTAR A; TEMPOL is paramagnetic radical used in NMR as SPIN LABELS whereas TEMPOL-H is not. 4-hydroxy-TEMPO : A member of the class of aminoxyls that is TEMPO carrying a hydroxy substituent at position 4. It is a radical scavenger which exhibits anti-inflammatory and analgesic properties.		1.9910
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		2.0210amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
tempidon
2,2,6,6-tetramethyl-4-piperidinone: structure in first source		1.9910piperidones
peroxynitric acid
[no description available]		2.420nitrogen oxoacid
lastar a
lastar A: RN given refers to parent cpd		1.9910
proxyl nitroxide
proxyl nitroxide: structure		1.9910aminoxyls;
pyrrolidines		radical scavenger
peroxynitrous acid
Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).		2.0210nitrogen oxoacid
3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-n-oxyl
3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl: a blood–brain barrier-permeative, redox-senstitive probe in electron paramagnetic resonance imaging		1.9910
tempol
[no description available]		1.9910aminoxyls;
hydroxypiperidine		anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
catalyst;
hepatoprotective agent;
nephroprotective agent;
neuroprotective agent;
radical scavenger
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		2.0410oxygen hydride;
oxygen radical;
reactive oxygen species
a 2545
A 2545: structure in first source		1.9910
2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid
2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid: structure given in first source		1.9910aminoxyls;
pyrrolidinecarboxylic acid
di-t-butyl nitroxide
di-tert-butyl nitroxide : An aminoxyl that is N-tert-butyl-2-methylpropan-2-amine carrying an oxidanediyl group at the nitrogen atom.		210aminoxylsspin label
triacetoneamine-n-oxyl
Triacetoneamine-N-Oxyl: Cyclic N-oxide radical functioning as a spin label and radiation-sensitizing agent.. 4-oxo-TEMPO : A member of the class of aminoxyls that is TEMPO carrying an oxo group at position 4.		2.730aminoxyls;
piperidones		radical scavenger
3-carbamoyl-2,2,5,5-tetramethyl-1-pyrrolidinyl-n-oxyl
3-carbamoyl-2,2,5,5-tetramethyl-1-pyrrolidinyl-N-oxyl: structure given in first source		1.9910aminoxyls;
pyrrolidinecarboxamide
3-carbamoyl-2,2,5,5-tetramethyl-3-pyrroline-1-yloxyl
[no description available]		1.9910
phenyl-n-tert-butylnitrone
phenyl-N-tert-butylnitrone: a spin-trapping agent		210
tempo
TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.		1.9910aminoxyls;
piperidines		catalyst;
ferroptosis inhibitor;
radical scavenger
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9910cysteiniumfundamental metabolite
piperidines
Piperidines: A family of hexahydropyridines.		3.150
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		1.9910ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
7,8-dihydroneopterin
7,8-dihydroneopterin: an antioxidant. 7,8-dihydroneopterin : A neopterin where positions C-7 and C-8 have been hydrogenated.		2.0210dihydropterin;
neopterins		Escherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
neopterin
[no description available]		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510