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SML1055

Sigma-Aldrich

3-AP-Me

≥98% (HPLC)

Synonym(s):

2-[(3-Amino-2-pyridinyl)methylene]-N,N-dimethyl-hydrazinecarbothioamide

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€85.90

About This Item

Empirical Formula (Hill Notation):
C9H13N5S
CAS Number:
1184391-57-8
Molecular Weight:
223.30
MDL number:
MFCD28124396
UNSPSC Code:
12352200
PubChem Substance ID:
329825641
NACRES:
NA.77

€85.90

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN(C)C(N/N=C/C1=C(N)C=CC=N1)=S

InChI

1S/C9H13N5S/c1-14(2)9(15)13-12-6-8-7(10)4-3-5-11-8/h3-6H,10H2,1-2H3,(H,13,15)/b12-6+

InChI key

DQVSEUUIXQTWRB-WUXMJOGZSA-N

Biochem/physiol Actions

3-AP-Me is a dimethyl derivative of the ribonucleotide reductase inhibitor 3-AP (SML0568). 3-AP-Me is a potent inducer of ER stress and the unfolded protein response in cancer cell lines, incuding IRE1, PERK and ATF6 activity. Treatment with 3-AP-Me induces CHOP expression, phosphorylation of eIF2α, up-regulation of ATF4 and Bim, and causes mitochondrial membrane depolarization and apoptosis.
3-AP-Me is a potent inducer of ER stress.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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

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Certificates of Analysis (COA)

Lot/Batch Number
054M4619V

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Articles

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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