Protoemetine

Base Information

• Chemical Name: Protoemetine
• CAS No.: 549-91-7
• Molecular Formula: C19H27 N O3
• Molecular Weight: 317.428
• DSSTox Substance ID: DTXSID30332083
• Nikkaji Number: J15.491A
• Wikidata: Q27108100
• Metabolomics Workbench ID: 69766
• Mol file: 549-91-7.mol

Synonyms:protoemetine

Chemical Property of Protoemetine

Chemical Property:

• PSA: 38.77000
• LogP: 3.17600
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 317.19909372
• Heavy Atom Count: 23
• Complexity: 402

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC3=CC(=C(C=C3C2CC1CC=O)OC)OC
• Isomeric SMILES: CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1CC=O)OC)OC
• Description: An oily base obtained from the bark of Cephaelis Ipecacuanha (Brot) A. Rich, the alkaloid is characterized as the perchlorate which forms crystals of the monohydrate from aqueous EtOH, m.p. 140-2°C or 193-5°C (dry). This salt has [α]D - 10.9° (c 3.13, EtOH) and gives an ultraviolet spectrum in ethanol with two absorption maxima at 232 and 283 mJ1. The base contains a formylmethyl group and yields a crystalline semicarbazone, m.p. 168-9°C. The optically inactive base has been synthesized and is also a colourless oil, giving a semicarbazone, m.p. 185-6°C.

Technology Process of Protoemetine

There total 29 articles about Protoemetine 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: 100.0%

3α-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxy-2β-<2,2-(propane-1,3-dithio)-ethyl>11bαH-benzoquinolizine hydrochloride → (+/-)-protoemetine (549-91-7,17132-38-6)

Guidance literature:

With water; methyl iodide; In acetonitrile; for 16h; Ambient temperature;

Reference yield: 92.0%

(-)-protoemetinol (7344-78-7) → (-)-Protoemetine (549-91-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/chem.201102012

Reference yield: 90.0%

(+/-)-(3c-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2t-yl)-acetic acid methyl ester (3332-90-9,3851-29-4,4185-35-7,38839-27-9,41645-79-8,68780-88-1) → (+/-)-protoemetine (549-91-7,17132-38-6)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1016/0040-4039(84)80026-X

upstream raw materials:

(-)-protoemetinol

(-)-(2R,3R,11bS)-2-(2-Benzyloxyethyl)-3-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxy-11bH-benzoquinolizidine

C₁₅H₁₈O₅

C₁₉H₂₆O₆

Downstream raw materials:

isoemetine

emetine

Refernces

• 1、 Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando. "Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine". supporting information; experimental part. p. 398 - 408. Retrieved 2012/02/16.
• 2、 Sun, Xuefeng,Ma, Dawei. "Organocatalytic approach for the syntheses of corynantheidol, dihydrocorynantheol, protoemetinol, protoemetine, and mitragynine". experimental part. p. 2158 - 2165. Retrieved 2011/10/18.