Emetine

Base Information

• Chemical Name: Emetine
• CAS No.: 483-18-1
• Deprecated CAS: 24377-67-1,888715-16-0
• Molecular Formula: C₂₉H₄₀N₂O₄
• Molecular Weight: 480.648
• European Community (EC) Number: 207-592-1,206-259-8
• UNII: X8D5EPO80M
• DSSTox Substance ID: DTXSID5022980
• Nikkaji Number: J9.377G
• Wikipedia: Emetine
• Wikidata: Q3050386
• NCI Thesaurus Code: C81578
• Pharos Ligand ID: CQQXUUU6S355
• Metabolomics Workbench ID: 53152
• ChEMBL ID: CHEMBL50588
• Mol file: 483-18-1.mol

Synonyms:Dihydrochloride, Emetine;Emetine;Emetine Dihydrochloride;Emetine Hydrochloride;Hydrochloride, Emetine;Ipecine;Methylcephaeline

Chemical Property of Emetine

Chemical Property:

• Melting Point: 89-96°C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 600.3°Cat760mmHg
• PKA: 5.77, 6.64(at 25℃)
• Flash Point: 316.9°C
• PSA: 52.19000
• Density: 1.17g/cm³
• LogP: 6.01210
• Storage Temp.: -20?C Freezer
• Solubility.: Soluble in Water (100 mg/ml)
• Water Solubility.: 961.3mg/L(15 oC)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 480.29880776
• Heavy Atom Count: 35
• Complexity: 679

Purity/Quality:

99%, ^*data from raw suppliers

Emetine(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion.
• Hazard Codes: Toxic by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Description: Emetine hydrochloride (483-18-1) is one of the active ingredients of ipecac root extract, used as an emetic.1 Induces apoptosis in breast cancer cells via inhibition of Wnt/β-catenin signaling.2 Inhibits Zika and Ebola virus in vitro and in vivo, targeting viral entry and replication by inhibiting viral RNA polymerase and host lysosomal function.3 Also inhibits SARS-CoV-2 replication in cells (EC50 for viral load reduction is 0.46 μM).4 A useful agent for inhibiting protein synthesis in eukaryotic cells by virtue of its inhibition of the ribosome 40S subunit.5
• Uses: Emetine is the principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha. Emetine occurs in the ground roots ofipecac (Uragoga ipecacuanha, Cephaelisipecacuanha, Uragoga acuminata, and Rubiaceae). Ipecacs are of two varieties, Brazilianand Cartagena. The former contains about1.2–1.5% emetine, and the latter constitutesabout 1.1–1.4% emetine. It is used as anemetic to induce vomiting for the treatmentof poisoning. It is also used as an antiamebic.
• Indications: Chlorprothixene (Taractan) has been reported twice to be effective in the treatment of PHN. For severe pain, an initial 50 to 100 mg IM injection has been advocated. Otherwise, the dosage is 25 to 50 mg PO q6h. The recommended duration of therapy is 4 to 10 days. Higher doses are unwarranted and frequently result in side effects.

Technology Process of Emetine

There total 33 articles about Emetine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

N-Pent-4-enoylemetine (163926-93-0) → emetine (483-18-1,522-99-6,7005-82-5,38241-16-6,65910-27-2,74059-23-7,74111-75-4,74111-76-5)

Guidance literature:

With iodine; In tetrahydrofuran; water;

DOI:10.1021/ja00116a047

Reference yield: 72.0%

(-)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline (523-01-3) → emetine (483-18-1,522-99-6,7005-82-5,38241-16-6,65910-27-2,74059-23-7,74111-75-4,74111-76-5)

Guidance literature:

With formic acid; triethylamine; Cl[(1S,2S)-N-p-Ts-1,2-diphenylethanediamine](p-cymene)Ru(II); In N,N-dimethyl-formamide; at 20 ℃; for 3.3h;

DOI:10.1021/ol0530326

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → emetine (483-18-1,522-99-6,7005-82-5,38241-16-6,65910-27-2,74059-23-7,74111-75-4,74111-76-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / AlMe₃ / benzene / 10 h / 115 °C

2: 75 percent / POCl₃ / benzene / 3.8 h / 110 °C

3: 72 percent / HCO₂H; Et₃N / Cl[(1S,2S)-N-p-Ts-1,2-diphenylethanediamine](p-cymene)Ru(II) / dimethylformamide / 3.3 h / 20 °C

With formic acid; trimethylaluminum; triethylamine; trichlorophosphate; Cl[(1S,2S)-N-p-Ts-1,2-diphenylethanediamine](p-cymene)Ru(II); In N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol0530326

upstream raw materials:

cephaeline

diazomethane

(+-)-Emetin

trimethylphenylammonium hydroxide

Downstream raw materials:

2-methoxy-phenol

trimethylamine

2'-Benzoyl-10,11,6',7'-tetramethoxy-emetan

rac-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide

Refernces

• 1、 Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando. "Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine". . p. 398 - 408. Retrieved 2012/02/16.
• 2、 -. "Compounds and compositions for treating infection". . . Retrieved 2009/04/24.