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188549

Sigma-Aldrich

2-Mercaptopyridine N-oxide

99%

Synonym(s):

2-Pyridinethiol-1-oxide, Pyrithione

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About This Item

Empirical Formula (Hill Notation):
C5H5NOS
CAS Number:
1121-31-9
Molecular Weight:
127.16
Beilstein:
109936
EC Number:
214-329-4
MDL number:
MFCD00006196
UNSPSC Code:
12352100
PubChem Substance ID:
24851166
NACRES:
NA.22

Assay

99%

mp

69-72 °C (lit.)

SMILES string

[O-][n+]1ccccc1S

InChI

1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H

InChI key

FGVVTMRZYROCTH-UHFFFAOYSA-N

General description

2-Mercaptopyridine N-oxide forms complexes on reaction with palladium chloride. It inhibits NADH-fumarate reductase purified from Trypanosoma cruzi. It is precursor to O-acyl thiohydroxamates. It ligates to metals to form biologically active complexes.

Application

2-Mercaptopyridine N-oxide was used to investigate the mechanism of photodegradation of mercaptopyridine-N-oxide biocides. It was used in ratiometric fluorescence imaging of intracellular zinc ions in mammalian cultures.
Precursor to O-acyl thiohydroxamates. Ligates to metals to form biologically active complexes.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000371407
0000371407
0000273822
0000273823
0000201097

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Vesna Lavtizar et al.
Ecotoxicology and environmental safety, 147, 132-138 (2017-08-26)
Copper pyrithione (CuPT) is a biocide, used worldwide to prevent biofouling on submerged surfaces. In aquatic environments it rapidly degrades, however, one of the degradation products (HPT) is known to react with cupric ion back to its parent compound. Not
Christopher J Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(5), 1129-1134 (2004-01-22)
Zinc is an essential metal ion for human growth and development, the disruption of cellular Zn(2+) homeostasis being implicated in several major disorders including Alzheimer's disease, diabetes, and cancer. The molecular mechanisms of Zn(2+) physiology and pathology are insufficiently understood
Matias Butler et al.
Journal of mass spectrometry : JMS, 52(11), 728-738 (2017-07-26)
2-Mercaptopyridine N-oxide (pyrithione, PTOH) along with several transition metal ions forms coordination compounds displaying notable biological activities. Gas-phase complexes formed between pyrithione and manganese (II), cobalt (II), nickel (II), copper (II), and zinc (II) were investigated by infusion in the
Photodegradation of mercaptopyridine-N-oxide biocides.
R A Neihof et al.
Archives of environmental contamination and toxicology, 8(3), 355-368 (1979-01-01)
J F Turrens et al.
FEMS microbiology letters, 175(2), 217-221 (1999-07-01)
The enzyme NADH-fumarate reductase is not found in mammalian cells but it is present in several parasitic protozoa including Trypanosoma cruzi, the parasite that causes Chagas' disease. This study shows that the drug 2-mercaptopyridine-N-oxide (MPNO) inhibits NADH-fumarate reductase purified from
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