E2375

Emetine dihydrochloride

Name: Emetine dihydrochloride
Brand: SIGMA

RNA polymerase inhibitor

Synonym(s):

6′,7′,10,11-Tetramethoxyemetan dihydrochloride

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All Photos(3)

About This Item

Empirical Formula (Hill Notation):

C₂₉H₄₀N₂O₄ · 2HCl

CAS Number:

316-42-7

Molecular Weight:

553.56

UNSPSC Code:

12352200

PubChem Substance ID:

24278410

NACRES:

NA.77

MDL number:

MFCD00242944

Product Name

Emetine dihydrochloride,

SMILES string

[H][C@@]12C[C@H](C[C@@]3([H])NCCC4=C3C=C(OC)C(OC)=C4)[C@@H](CC)CN1CCC5=C2C=C(OC)C(OC)=C5

InChI

1S/C29H40N2O4.2ClH/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24;;/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3;2*1H/t18-,21-,24+,25-;;/m0../s1

InChI key

JROGBPMEKVAPEH-GXGBFOEMSA-N

antibiotic activity spectrum

parasites

mode of action

protein synthesis | interferes

storage temp.

2-8°C

Quality Level

100

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Emetine dihydrochloride has been used:

as a protein synthesis inhibitor to study its effects on human papillomavirus type 8 E2 protein half-life
to study its effects on the stress granules assembly
as a chain-elongation inhibitor in puromycin assay for protein synthesis

Biochem/physiol Actions

Emetine dihydrochloride is a member of the ipecac alkaloids family. It can mediate inhibition of protein and nucleic acid synthesis. It exhibits antiviral activity against dengue virus infection and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). Emetine dihydrochloride exhibits anti-proliferative effects against bladder cancer cells. It also possesses anti-protozoal activity.

Features and Benefits

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

pictograms

GHS06

signalword

Danger

hcodes

H300,H315,H319

pcodes

P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338 - P332 + P313

Hazard Classifications

Acute Tox. 1 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Antiviral activity of emetine dihydrochloride against dengue virus infection

Yin L J S, et al.

Journal of Antivirals & Antiretrovirals, 1, 062-000 (2009)

Comparison of membrane proteins of Mycobacterium tuberculosis H37Rv and H37Ra strains.

Hiwa Målen et al.

BMC microbiology, 11, 18-18 (2011-01-26)

The potential causes for variation in virulence between distinct M. tuberculosis strains are still not fully known. However, differences in protein expression are probably an important factor. In this study we used a label-free quantitative proteomic approach to estimate differences

Intermittent fasting promotes prolonged associative interactions during synaptic tagging/capture by altering the metaplastic properties of the CA1 hippocampal neurons.

Ananya Dasgupta et al.

Neurobiology of learning and memory, 154, 70-77 (2017-12-27)

Metaplasticity is the inherent property of a neuron or neuronal population to undergo activity-dependent changes in neural function that modulate subsequent synaptic plasticity. Here we studied the effect of intermittent fasting (IF) in governing the interactions of associative plasticity mechanisms

Induction of apoptosis and changes in nuclear G-actin are mediated by different pathways: the effect of inhibitors of protein and RNA synthesis in isolated rat hepatocytes.

I Meijerman et al.

Toxicology and applied pharmacology, 156(1), 46-55 (1999-04-02)

Stressor-induced changes in the cytoskeleton, of which actin is a major component, may lead to apoptosis. The role of drug-induced changes in nuclear G-actin and apoptosis was studied in freshly isolated hepatocytes. Several protein synthesis inhibitors, cycloheximide, puromycin, and emetine

TDP-43 is recruited to stress granules in conditions of oxidative insult.

Claudia Colombrita et al.

Journal of neurochemistry, 111(4), 1051-1061 (2009-09-22)

Transactive response DNA-binding protein 43 (TDP-43) forms abnormal ubiquitinated and phosphorylated inclusions in brain tissues from patients with amyotrophic lateral sclerosis (ALS) and frontotemporal lobar degeneration. TDP-43 is a DNA/RNA-binding protein involved in RNA processing, such as transcription, pre-mRNA splicing

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