Skip to Content
Merck
All Photos(5)

Key Documents

A3509

Sigma-Aldrich

2-Aminopurine

≥99%

Synonym(s):

2-AP

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C5H5N5
CAS Number:
Molecular Weight:
135.13
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

Assay

≥99%

form

powder

mp

280-282 °C (lit.)

storage temp.

2-8°C

SMILES string

Nc1ncc2[nH]cnc2n1

InChI

1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)

InChI key

MWBWWFOAEOYUST-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

2-Aminopurine (2-AP) is used to specifically inhibit double-stranded RNA-dependent protein kinase, protein kinase R (PKR).
2-Aminopurine has been used to inhibit eukaryotic initiation factor-2α (eIF2α)-phosphorylation of osteoarthritis (OA) chondrocytes.

Biochem/physiol Actions

2-Aminopurine (2AP) is an analog of guanosine and adenosine, which can base pair with cytosine and thymine. It is used as a fluorescent probe in nucleic acid structure and dynamics. 2-Aminopurine (2-AP) inhibits double-stranded RNA-dependent protein kinase, protein kinase R (PKR).

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Double-Stranded RNA-Dependent Protein Kinase Is Involved in 2-Methoxyestradiol?Mediated Cell Death of Osteosarcoma Cells
Shogren KL, et al.
Journal of Bone and Mineral Research, 22(1), 29-36 (2007)
2-Aminopurine fluorescence quenching and lifetimes: role of base stacking
Jean JM and Hall KB
Proceedings of the National Academy of Sciences of the USA, 98(1), 37-41 (2001)
Danqing Xin et al.
Brain, behavior, and immunity, 73, 222-234 (2018-05-12)
We previously reported that l-Cysteine, an H2S donor, significantly alleviated brain injury after hypoxia-ischemic (HI) injury in neonatal mice. However, the mechanisms underlying this neuroprotective effect of l-Cysteine against HI insult remain unknown. In the present study, we tested the
2-Aminopurine.
A Ronen
Mutation research, 75(1), 1-47 (1980-01-01)
Julien Godet et al.
Nucleic acids research, 41(9), 5036-5048 (2013-03-21)
The HIV-1 nucleocapsid protein (NCp7) is a nucleic acid chaperone required during reverse transcription. During the first strand transfer, NCp7 is thought to destabilize cTAR, the (-)DNA copy of the TAR RNA hairpin, and subsequently direct the TAR/cTAR annealing through

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service