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MedKoo Cat#: 564858 | Name: Emetine free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Emetine free base
Emetine free base
CAS#483-18-1 (free base)

Theoretical Analysis

MedKoo Cat#: 564858

Name: Emetine free base

CAS#: 483-18-1 (free base)

Chemical Formula: C29H40N2O4

Exact Mass: 480.2988

Molecular Weight: 480.65

Elemental Analysis: C, 72.47; H, 8.39; N, 5.83; O, 13.31

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 weeks
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Related CAS #
316-42-7 (2HCl) 483-18-1 (free base) 2228-39-9 (2HCl) 7083-71-8 (HCl hydrate)
Synonym
Emetine; Emetine free base;
IUPAC/Chemical 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
InChi Key
AUVVAXYIELKVAI-CKBKHPSWSA-N
InChi Code
InChI=1S/C29H40N2O4/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/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
Appearance
Solid powder
Purity
>90% (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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 480.65 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
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.