Structure via PubChem · Public domain (PubChem)
emetine
Sign in to saveAlso known as cephaeline methyl ether, methyl cephaeline, emetin
Emetine is a drug used as both an anti-protozoal and to induce vomiting. It is produced from the ipecac root. It takes its name from its emetic properties.
Chemical data
- Formula
- C29H40N2O4
- Molecular weight
- 480.6 g/mol
- IUPAC name
- (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
- SMILES
- CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
- InChIKey
- AUVVAXYIELKVAI-CKBKHPSWSA-N
- XLogP
- 4.7
- Polar surface area
- 52.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
2,291 papers- Emetine, a small molecule natural product, displays potent anti-gastric cancer activity via regulation of multiple signaling pathways.Cancer chemotherapy and pharmacology · 2023
- Emetine blocks DNA replication via proteosynthesis inhibition not by targeting Okazaki fragments.Life science alliance · 2022
- Emetine protects mice from enterovirus infection by inhibiting viral translation.Antiviral research · 2020
- Mechanism of emetine cardiotoxicity.Pharmacology & therapeutics · 1980
- Spectroscopic Investigation of Emetine-DNA Binding.Journal of medicinal chemistry · 2025
via PubMed
Wikidata facts
- Mass
- 480.299
Show 5 more facts
- chemical formula
- C₂₉H₄₀N₂O₄
- canonical SMILES
- CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
- isomeric SMILES
- CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
- Commons category
- Emetine
- defined daily dose
- 60
via Wikidata · CC0
~5 min read
Article
9 sectionsContents
- Early preparations
- Use as anti-amoebic
- Dehydroemetine
- Cephaeline
- Use in blocking protein synthesis
- Biosynthesis
- Side effects
- Research
- References
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| tradename = | Drugs.com = | pregnancy_AU = | pregnancy_US = | legal_AU = | legal_CA = | legal_UK = | legal_US =