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M6875

Sigma-Aldrich

2-Mercaptopurine

≥95%, crystalline

Synonym(s):

2-MP, 2-Purinethiol, 2-Thiopurine

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About This Item

Empirical Formula (Hill Notation):
C5H4N4S
CAS Number:
28128-19-0
Molecular Weight:
152.18
EC Number:
248-855-0
MDL number:
MFCD00047145
UNSPSC Code:
41106305
PubChem Substance ID:
24897120
NACRES:
NA.51

Quality Level

100

Assay

≥95%

form

crystalline

color

yellow

solubility

1 M NH4OH: 50 mg/mL, clear to slightly hazy, yellow to brown

SMILES string

[H]n1cnc2cnc(S)nc12

InChI

1S/C5H4N4S/c10-5-6-1-3-4(9-5)8-2-7-3/h1-2H,(H2,6,7,8,9,10)

InChI key

HDBQZGJWHMCXIL-UHFFFAOYSA-N

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Application

2-Mercaptopurine (2-MP), a thiopurine and analog of the anti-cancer drug 6-mercaptopurine (6-MP), has been used to study the substrate and binding specificity and kinetics of xanthine oxidase-catalyzed hydroxylation and myeloperoxidase (MPO) reactions. 2-Mercaptopurine inhibited lipopolysacharide (LPS)-dependent nitric oxide (NO) production in B cells.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 - H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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U Burner et al.
FEBS letters, 443(3), 290-296 (1999-02-20)
Myeloperoxidase (MPO) is the most abundant protein in neutrophils and plays a central role in microbial killing and inflammatory tissue damage. Because most of the non-steroidal anti-inflammatory drugs and other drugs contain a thiol group, it is necessary to understand
Xi Chen et al.
Protein & cell, 10(5), 327-346 (2018-08-22)
Primitive mammalian heart transforms from a single tube to a four-chambered muscular organ during a short developmental window. We found that knocking out global microRNA by deleting Dgcr8 microprocessor in Mesp1 cardiovascular progenitor cells lead to the formation of extremely
Mohammad Amin Safari et al.
International journal of environmental research and public health, 17(18) (2020-09-18)
This study assessed the effect of swimming training on anxiety-like behaviors and corticosterone. Thirty adult male Wistar rats were randomly assigned to five study conditions: swimming training (ST); exposure to chronic mild stress (CS); exposure to chronic mild stress followed
Hemlata Tamta et al.
Biochemistry. Biokhimiia, 72(2), 170-177 (2007-03-21)
Xanthine oxidase-catalyzed hydroxylation reactions of the anticancer drug 6-mercaptopurine (6-MP) and its analog 2-mercaptopurine (2-MP) as well as 6-thioxanthine (6-TX) and 2-thioxanthine (2-TX) have been studied using UV-spectroscopy, high pressure liquid chromatography, photodiode array, and liquid chromatography-based mass spectral analysis.
S Hortelano et al.
Molecular pharmacology, 51(3), 414-421 (1997-03-01)
6-Mercaptopurine and related purine antimetabolites are used in the treatment of several B cell disorders. These drugs inhibited the proliferation of mature splenic B cells after being triggered with polyclonal mitogens. In addition to the antiproliferative effects, 6-mercaptopurine, 2-mercaptopurine, and
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