Emetine HCl
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MedKoo CAT#: 531018

CAS#: 316-42-7 (HCl)

Description: 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. Emetine protects mice from enterovirus infection by inhibiting viral translation. Emetine Synergizes with Cisplatin to Enhance Anti-Cancer Efficacy against Lung Cancer Cells. Emetine exhibits anticancer activity in breast cancer cells as an antagonist of Wnt/β‑catenin signaling. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibiting viral replication and decreasing viral entry.


Chemical Structure

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Emetine HCl
CAS# 316-42-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 531018
Name: Emetine HCl
CAS#: 316-42-7 (HCl)
Chemical Formula: C29H42Cl2N2O4
Exact Mass: 0.00
Molecular Weight: 553.565
Elemental Analysis: C, 62.92; H, 7.65; Cl, 12.81; N, 5.06; O, 11.56

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to Ship
100mg USD 1650 Ready to Ship
200mg USD 2950 Ready to Ship
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Related CAS #: 316-42-7 (HCl)   483-18-1 (free base)   2228-39-9 (2HCl)   7083-71-8 (HCl hydrate)    

Synonym: Emetine hydrochloride, Dehydroemetine dihydrochloride, Emetine, Amebicide, Purum

IUPAC/Chemical Name: (2S,3R,11bS)-2-(((R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline dihydrochloride

InChi Key: JROGBPMEKVAPEH-GXGBFOEMSA-N

InChi Code: 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

SMILES Code: COC1=CC2=C(C=C1OC)CCN[C@@H]2C[C@@H]3[C@@H](CC)CN4CCC5=CC(OC)=C(OC)C=C5[C@]4([H])C3.[H]Cl.[H]Cl

Appearance: White to light yellow crystalline powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Safety Data Sheet (SDS):
Biological target: Emetine is a RNA polymerase inhibitor that inhibits SARS-CoV-2 replication (EC50 = 460 nM)
In vitro activity: To further investigate the mechanism of the effect of emetine on the Wnt pathway, 293T cells were transfected with a Wnt1 expression plasmid. Overexpression of Wnt1 resulted in enhanced levels of phosphorylated LRP6, total LRP6, DVL2, activated βcatenin and cytosolic β-catenin (Fig. 2). Treatment with nanomolar concentrations of emetine significantly decreased the expression levels of phosphorylated LRP6, total LRP6, phosphorylated DVL2, active β-catenin and cytosolic β-catenin (Fig. 2). Notably, the extent of reduction in total and phosphorylated LRP6 was similar upon emetine treatment, suggesting that emetine may downregulate LRP6 expression, but not its phosphorylation. These findings indicated that emetine inhibits Wnt/β-catenin signaling by targeting LPR6 and DVL2. Reference: Oncol Rep. 2019 Nov; 42(5): 1735–1744. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6775799/
In vivo activity: In order to confirm the anti-leukemia activity of emetine, AML-bearing immunodeficient NSG mice were treated daily with the vehicle control or emetine (1 mg/kg weight) for 7 days, starting 7 days after transplantation when the leukemia was already established in the recipient mouse. At day 21, mice were analyzed for the presence of human AML cells in the bone marrow. Mice were left untreated 7 days after finishing the treatment regimen to allow AML cells to regenerate the disease. A significant reduction in the frequency of human AML cells in bone marrow was observed in emetine-treated mice compared to vehicle-control treated mice (Figure5B). In fact, the colonies generated from emetine-treated engrafted human leukemia bone marrow cells displayed a reduced cellularity as compared to control samples (Figure5C). Taken together, emetine reduced both leukemia burden in vivo and the clonogenic capacity of leukemic cells upon treatment. Reference: Oncotarget. 2016 Apr 26; 7(17): 23239–23250. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5029623/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 55.4 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 553.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Sun Q, Fu Q, Li S, Li J, Liu S, Wang Z, Su Z, Song J, Lu D. Emetine exhibits anticancer activity in breast cancer cells as an antagonist of Wnt/β‑catenin signaling. Oncol Rep. 2019 Nov;42(5):1735-1744. doi: 10.3892/or.2019.7290. Epub 2019 Aug 22. PMID: 31436297; PMCID: PMC6775799. 2. Cornet-Masana JM, Moreno-Martínez D, Lara-Castillo MC, Nomdedeu M, Etxabe A, Tesi N, Pratcorona M, Esteve J, Risueño RM. Emetine induces chemosensitivity and reduces clonogenicity of acute myeloid leukemia cells. Oncotarget. 2016 Apr 26;7(17):2323950. doi: 10.18632/oncotarget.8096. PMID: 26992240; PMCID: PMC5029623. 3. Aoki T, Shimada K, Sakamoto A, Sugimoto K, Morishita T, Kojima Y, Shimada S, Kato S, Iriyama C, Kuno S, Harada Y, Tomita A, Hayakawa F, Kiyoi H. Emetine elicits apoptosis of intractable B-cell lymphoma cells with MYC rearrangement through inhibition of glycolytic metabolism. Oncotarget. 2017 Feb 21;8(8):13085-13098. doi: 10.18632/oncotarget.14393. PMID: 28055963; PMCID: PMC5355079.
In vitro protocol: 1. Sun Q, Fu Q, Li S, Li J, Liu S, Wang Z, Su Z, Song J, Lu D. Emetine exhibits anticancer activity in breast cancer cells as an antagonist of Wnt/β‑catenin signaling. Oncol Rep. 2019 Nov;42(5):1735-1744. doi: 10.3892/or.2019.7290. Epub 2019 Aug 22. PMID: 31436297; PMCID: PMC6775799. 2. Cornet-Masana JM, Moreno-Martínez D, Lara-Castillo MC, Nomdedeu M, Etxabe A, Tesi N, Pratcorona M, Esteve J, Risueño RM. Emetine induces chemosensitivity and reduces clonogenicity of acute myeloid leukemia cells. Oncotarget. 2016 Apr 26;7(17):2323950. doi: 10.18632/oncotarget.8096. PMID: 26992240; PMCID: PMC5029623.
In vivo protocol: 1. Cornet-Masana JM, Moreno-Martínez D, Lara-Castillo MC, Nomdedeu M, Etxabe A, Tesi N, Pratcorona M, Esteve J, Risueño RM. Emetine induces chemosensitivity and reduces clonogenicity of acute myeloid leukemia cells. Oncotarget. 2016 Apr 26;7(17):2323950. doi: 10.18632/oncotarget.8096. PMID: 26992240; PMCID: PMC5029623. 2. Aoki T, Shimada K, Sakamoto A, Sugimoto K, Morishita T, Kojima Y, Shimada S, Kato S, Iriyama C, Kuno S, Harada Y, Tomita A, Hayakawa F, Kiyoi H. Emetine elicits apoptosis of intractable B-cell lymphoma cells with MYC rearrangement through inhibition of glycolytic metabolism. Oncotarget. 2017 Feb 21;8(8):13085-13098. doi: 10.18632/oncotarget.14393. PMID: 28055963; PMCID: PMC5355079.

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1: Bleasel MD, Peterson GM. Emetine, Ipecac, Ipecac Alkaloids and Analogues as Potential Antiviral Agents for Coronaviruses. Pharmaceuticals (Basel). 2020 Mar 21;13(3):E51. doi: 10.3390/ph13030051. PMID: 32245264.

2: Wu TH, Chang SY, Shih YL, Huang TW, Chang H, Lin YW. Emetine Synergizes with Cisplatin to Enhance Anti-Cancer Efficacy against Lung Cancer Cells. Int J Mol Sci. 2019 Nov 25;20(23):5914. doi: 10.3390/ijms20235914. PMID: 31775307; PMCID: PMC6928603.

3: Tang Q, Li S, Du L, Chen S, Gao J, Cai Y, Xu Z, Zhao Z, Lan K, Wu S. Emetine protects mice from enterovirus infection by inhibiting viral translation. Antiviral Res. 2020 Jan;173:104650. doi: 10.1016/j.antiviral.2019.104650. Epub 2019 Nov 14. PMID: 31734270.

4: Alam N, Yu JQ, Beale P, Huq F. Dose and Sequence Dependent Synergism from the Combination of Oxaliplatin with Emetine and Patulin against Colorectal Cancer. Anticancer Agents Med Chem. 2019 Oct 21. doi: 10.2174/1871520619666191021112042. Epub ahead of print. PMID: 31736447.

5: Andersen PI, Krpina K, Ianevski A, Shtaida N, Jo E, Yang J, Koit S, Tenson T, Hukkanen V, Anthonsen MW, Bjoras M, Evander M, Windisch MP, Zusinaite E, Kainov DE. Novel Antiviral Activities of Obatoclax, Emetine, Niclosamide, Brequinar, and Homoharringtonine. Viruses. 2019 Oct 18;11(10):964. doi: 10.3390/v11100964. PMID: 31635418; PMCID: PMC6832696.

6: Siddique MAH, Satoh K, Kurosawa R, Kikuchi N, Elias-Al-Mamun M, Omura J, Satoh T, Nogi M, Sunamura S, Miyata S, Ueda H, Tokuyama H, Shimokawa H. Identification of Emetine as a Therapeutic Agent for Pulmonary Arterial Hypertension: Novel Effects of an Old Drug. Arterioscler Thromb Vasc Biol. 2019 Nov;39(11):2367-2385. doi: 10.1161/ATVBAHA.119.313309. Epub 2019 Sep 19. PMID: 31533472.

7: Sun Q, Fu Q, Li S, Li J, Liu S, Wang Z, Su Z, Song J, Lu D. Emetine exhibits anticancer activity in breast cancer cells as an antagonist of Wnt/β‑catenin signaling. Oncol Rep. 2019 Nov;42(5):1735-1744. doi: 10.3892/or.2019.7290. Epub 2019 Aug 22. PMID: 31436297; PMCID: PMC6775799.

8: Gallegos-Gómez ML, Greotti E, López-Méndez MC, Sánchez-Vázquez VH, Arias JM, Guerrero-Hernández A. The Trans Golgi Region is a Labile Intracellular Ca2+ Store Sensitive to Emetine. Sci Rep. 2018 Nov 21;8(1):17143. doi: 10.1038/s41598-018-35280-z. PMID: 30464185; PMCID: PMC6249204.

9: MacGibeny MA, Koyuncu OO, Wirblich C, Schnell MJ, Enquist LW. Retrograde axonal transport of rabies virus is unaffected by interferon treatment but blocked by emetine locally in axons. PLoS Pathog. 2018 Jul 20;14(7):e1007188. doi: 10.1371/journal.ppat.1007188. PMID: 30028873; PMCID: PMC6070286.

10: Yang S, Xu M, Lee EM, Gorshkov K, Shiryaev SA, He S, Sun W, Cheng YS, Hu X, Tharappel AM, Lu B, Pinto A, Farhy C, Huang CT, Zhang Z, Zhu W, Wu Y, Zhou Y, Song G, Zhu H, Shamim K, Martínez-Romero C, García-Sastre A, Preston RA, Jayaweera DT, Huang R, Huang W, Xia M, Simeonov A, Ming G, Qiu X, Terskikh AV, Tang H, Song H, Zheng W. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibiting viral replication and decreasing viral entry. Cell Discov. 2018 Jun 5;4:31. doi: 10.1038/s41421-018-0034-1. PMID: 29872540; PMCID: PMC5986771.

11: Nieto A, Pérez Ishiwara DG, Orozco E, Sánchez Monroy V, Gómez García C. A Novel Heat Shock Element (HSE) in Entamoeba histolytica that Regulates the Transcriptional Activation of the EhPgp5 Gene in the Presence of Emetine Drug. Front Cell Infect Microbiol. 2017 Nov 29;7:492. doi: 10.3389/fcimb.2017.00492. PMID: 29238701; PMCID: PMC5712549.

12: Akinboye ES, Rosen MD, Bakare O, Denmeade SR. Anticancer activities of emetine prodrugs that are proteolytically activated by the prostate specific antigen (PSA) and evaluation of in vivo toxicity of emetine derivatives. Bioorg Med Chem. 2017 Dec 15;25(24):6707-6717. doi: 10.1016/j.bmc.2017.11.015. Epub 2017 Nov 10. PMID: 29153549; PMCID: PMC6003237.

13: Khandelwal N, Chander Y, Rawat KD, Riyesh T, Nishanth C, Sharma S, Jindal N, Tripathi BN, Barua S, Kumar N. Emetine inhibits replication of RNA and DNA viruses without generating drug-resistant virus variants. Antiviral Res. 2017 Aug;144:196-204. doi: 10.1016/j.antiviral.2017.06.006. Epub 2017 Jun 15. PMID: 28624461.

14: Busonero C, Leone S, Acconcia F. Emetine induces estrogen receptor alpha degradation and prevents 17β-estradiol-induced breast cancer cell proliferation. Cell Oncol (Dordr). 2017 Jun;40(3):299-301. doi: 10.1007/s13402-017-0322-z. Epub 2017 Mar 29. PMID: 28357567.

15: Matthews H, Deakin J, Rajab M, Idris-Usman M, Nirmalan NJ. Investigating antimalarial drug interactions of emetine dihydrochloride hydrate using CalcuSyn-based interactivity calculations. PLoS One. 2017 Mar 3;12(3):e0173303. doi: 10.1371/journal.pone.0173303. PMID: 28257497; PMCID: PMC5336292.

16: Aoki T, Shimada K, Sakamoto A, Sugimoto K, Morishita T, Kojima Y, Shimada S, Kato S, Iriyama C, Kuno S, Harada Y, Tomita A, Hayakawa F, Kiyoi H. Emetine elicits apoptosis of intractable B-cell lymphoma cells with MYC rearrangement through inhibition of glycolytic metabolism. Oncotarget. 2017 Feb 21;8(8):13085-13098. doi: 10.18632/oncotarget.14393. PMID: 28055963; PMCID: PMC5355079.

17: Krstin S, Mohamed T, Wang X, Wink M. How do the alkaloids emetine and homoharringtonine kill trypanosomes? An insight into their molecular modes of action. Phytomedicine. 2016 Dec 15;23(14):1771-1777. doi: 10.1016/j.phymed.2016.10.008. Epub 2016 Oct 14. PMID: 27912879.

18: Mukhopadhyay R, Roy S, Venkatadri R, Su YP, Ye W, Barnaeva E, Mathews Griner L, Southall N, Hu X, Wang AQ, Xu X, Dulcey AE, Marugan JJ, Ferrer M, Arav-Boger R. Efficacy and Mechanism of Action of Low Dose Emetine against Human Cytomegalovirus. PLoS Pathog. 2016 Jun 23;12(6):e1005717. doi: 10.1371/journal.ppat.1005717. PMID: 27336364; PMCID: PMC4919066.

19: Hudson LK, Dancho ME, Li J, Bruchfeld JB, Ragab AA, He MM, Bragg M, Lenaghan D, Quinn MD, Fritz JR, Tanzi MV, Silverman HA, Hanes WM, Levine YA, Pavlov VA, Olofsson PS, Roth J, Al-Abed Y, Andersson U, Tracey KJ, Chavan SS. Emetine Di- HCl Attenuates Type 1 Diabetes Mellitus in Mice. Mol Med. 2016 Oct;22:585-596. doi: 10.2119/molmed.2016.00082. Epub 2016 Jun 10. PMID: 27341452; PMCID: PMC5082289.

20: Uzor PF. Recent developments on potential new applications of emetine as anti-cancer agent. EXCLI J. 2016 May 10;15:323-8. doi: 10.17179/excli2016-280. PMID: 27366142; PMCID: PMC4928012.