Emetine
Compound Structure: |
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Synonyms: | (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; Emetin; Cephaeline methyl ether; Methyl cephaeline; 6',7',10,11-Tetramethoxyemetan; (-)-Emetine; Cephalin | ||||||||||||||||||||||||||||||||||||||||||||
Compound ID: | NMPC-1003 | ||||||||||||||||||||||||||||||||||||||||||||
PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||||
Molecular Formula: | C29H40N2O4 | ||||||||||||||||||||||||||||||||||||||||||||
Canonical SMILES: | CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC | ||||||||||||||||||||||||||||||||||||||||||||
InChIKey: | AUVVAXYIELKVAI-CKBKHPSWSA-N | ||||||||||||||||||||||||||||||||||||||||||||
About the compound: | Emetine is a pyridoisoquinoline derivative, consisting of emetam with methoxy substituents at the 6'-, 7'-, 10-, and 11-positions. It functions as an antiprotozoal agent and emetic, and is known for its ability to inhibit the replication of various viruses, including SARS-CoV-2, Zika, and Ebola. Additionally, emetine displays a range of medicinal properties including antimalarial, antineoplastic, and antiamoebic effects. In its roles as a pharmaceutical agent, emetine serves as an antiprotozoal drug, a plant metabolite, an antiviral agent, an emetic, a protein synthesis inhibitor, an antimalarial, an antineoplastic agent, an autophagy inhibitor, an anti-infective agent, an expectorant, an anticoronaviral agent, and an antiamoebic agent. Chemically, it belongs to the class of pyridoisoquinoline and isoquinoline alkaloids and is functionally related to cephaeline. It exists as a conjugate base of an emetine(2+), and is derived from a hydride of emetan. Emetine is the principal alkaloid found in ipecac, extracted from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, belonging to the Rubiaceae family. While it is used as an amebicide in various preparations, it's important to note that emetine can cause significant adverse effects, including serious cardiac, hepatic, or renal damage, along with severe diarrhea and vomiting. Its mechanism of action includes inhibiting protein synthesis in eukaryotic cells, but not prokaryotic cells. This distinction makes it an effective agent against certain parasites and viruses that affect eukaryotic cells. GHS Hazard Statements • H300 (97.62%): Fatal if swallowed [Danger Acute toxicity, oral] • H315 (95.24%): Causes skin irritation [Warning Skin corrosion/irritation] • H319 (95.24%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] • H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
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Properties: |
Chemical and Physical Properties
Source: PubChem |
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Source Species: |
Borreria verticillata. |