An alkaloid with diverse biological activities
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Emetine (hydrochloride hydrate)

Item No. 21048

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,11bS)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-2H-benzo[a]quinolizine, dihydrochloride, hydrate
CAS Number
7083-71-8
Molecular Formula
C29H40N2O4 • 2HCl [XH2O]
Formula Weight
553.6
Purity
≥85%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 1 mg/mlWater: 100 mg/ml
SMILES
CC[C@@H]1[C@@H](C[C@@]2(C3=CC(OC)=C(C=C3CCN2)OC)[H])C[C@]4(C5=CC(OC)=C(C=C5CCN4C1)OC)[H].Cl.Cl.O
InChi Code
InChI=1S/C29H40N2O4.2ClH.H2O/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;1H2/t18-,21-,24+,25-;;;/m0.../s1
InChi Key
IZTPMTAWOCEKKM-VXMYZLRESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    100 mg

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    Product Description

    Emetine is an alkaloid that has been found in ipecac root and has diverse biological activities.1,2,3,4 It is active against several strains of E. histolytica amoebae (IC50s = 0.73-10.22 μg/ml).1 Emetine inhibits NF-κB signaling induced by TNF-α or IL-1β (IC50s = 2 and 4.2 μM, respectively, in a cell-based β-lactamase reporter assay), increases caspase-3/7 activity in ME180 cells (EC50 = 1.1 μM), and is cytotoxic to HeLa cells.2 It reduces the infectious virus yield and viral RNA copy numbers in the culture supernatant of Vero E6 cells infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2; EC50s = 0.46 and 0.5 μM, respectively).4 Emetine (5 mg/kg) induces emesis in ferrets, an effect that can be prevented by the serotonin (5-HT) receptor subtype 5-HT3 antagonist ondansetron.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Burchard, G.D., and Mirelman, D. Entamoeba histolytica: Virulence potential and sensitivity to metronidazole and emetine of four isolates possessing nonpathogenic zymodemes. Exp. Parasitol. 66(2), 231-242 (1988).

    2. Miller, S.C., Huang, R., Sakamuru, S., et al. Identification of known drugs that act as inhibitors of NF-κB signaling and their mechanism of action. Biochem. Pharmacol. 79(9), 1272-1280 (2016).

    3. Hasegawa, M., Sasaki, T., Sadakane, K., et al. Studies for the emetic mechanisms of ipecac syrup (TJN-119) and its active components in ferrets: Involvement of 5-hydroxytryptamine receptors. Jpn. J. Pharmacol. 89(2), 113-119 (2002).

    4. Choy, K.-T., Wong, A.-Y., Kaewpreedee, P., et al. Remdesivir, lopinavir, emetine, and homoharringtonine inhibit SARS-CoV-2 replication in vitro. Antiviral Res. 178, 104786 (2020).