logging in or signing up EMETIN ELUCIDATION SEMINAR abdulrazzaqM.PHARM Download Post to : URL : Related Presentations : Let's Connect Share Add to Flag Embed Email Send to Blogs and Networks Add to Channel Copy embed code: Embed: Flash iPad Dynamic Copy Does not support media & animations Automatically changes to Flash or non-Flash embed WordPress Embed Customize Embed URL: Copy Thumbnail: Copy The presentation is successfully added In Your Favorites. Views: 295 Category: Science & Tech.. License: All Rights Reserved Like it (0) Dislike it (0) Added: November 10, 2010 This Presentation is Public Favorites: 0 Presentation Description No description available. Comments Posting comment... Premium member Presentation Transcript Slide 1: 1 MEDICINAL CHEMISTRY-II (NATURAL PRODUTS) Seminar on STRUCTURE ELUCIDATION OF EMETINE Presented by: Mr. ABDUL RAZZAQ M. Pharm. Department -: Pharmaceutical Chemistry Luqman College of Pharmacy Gulbarga. Slide 2: Points going to discuss are, 1. Introduction 2. Isolation 3. Properties 4. Constitution 5. Synthesis FOR EMETINE Slide 3: INTRODUCTION Emetine being an alkaloid was first isolated by Pelletier and Magendie in the year 1817 from roots of Cephalis ipecacuanha belonging to the family Rubiaceae. Slide 4: ISOLATION- Roots of iecacuanha & granadensis powder Agited with Ethyl Alco. Or Amyl alco. or Mix. Of Ben. & Lpetro. Decantation Residue Organic solvent + dil.HCl + NH3 Addition of ETHER Aqueous Liquid Ether Layer (Psychotrine alkaloids) (Remaining alkaloids containing EMETINE) Concentrated & convert into HCl salt Fractional Extraction EMETINE salts Remaining get converted gets crystallized out into oxalates Slide 5: PROPERTIES- White amorphous powder melting point 70°C. sparingly soluble in Water completely miscible in organic solvents like Alcohol, Chloroform and Ether. Uses- Emetic, Expectorant & Amoebic dysentery CONSTITUTION : CONSTITUTION Molecular formula- By analytical data it is found to be Emetine does not contain N-methyl groups but has a secondary and a tertiary nitrogen atoms. Presence of 4 methoxyl group- it is given by Zeisel Method where in on treating with hydroiodic acid this yields 4 molecules of methyl iodide showing presence of methoxyl groups. Presence of one unit of 6,7-dimethoxy isoquinoline- (a)oxidation with potassium permanganate in presence of acetone to give m-hemipinic acid(1) with small amounts of 6,7-dimethoxy,isoquinoline-1-carboxylic acid(2). Slide 7: (b) Oxidation with chromic acid- it yields 4,5-dimethoxy phthalonimide(3) Derivative of tetrahydro isoquinoline- this is shown by the UV-spectra of cephaline and emetine which resembles that of 1,2,3,4-tetrahydro isoquinoline Presence of o-dimethoxy benzene units- This is shown by the UV-spectra of emetine which closely resembles that of tetra hydro papaverine Further proof for 6,7-dimethoxy isoquinoline- (a)Gentle oxidation with alkaline potassium permanganate-this yields firstly Corydaldine(4) then when the remaining mother liquor is oxidized further with the permanganate it gives m-hemipinic acid(1) Slide 8: (b)Cephaeline another ipecac alkaloid on ethylation gives ethyl ether of cephaeline which yielded a mixture of corydaldine(4) and ethoxy methoxy isoquinoline (c) oxidation of emetine gives 96% yield of m-hemipinic acid which is higher when compared to papaverine this shows the presence of 2 isoquinoline units Partial structure of Emetine. : The nature of fragment this is given by Hoffmann Degradation of Emetine which removes the nitrogen atoms completely. It is given in the following steps. Slide 12: The formation of ketone is also shown as; The structure of (6) can also be given as; Slide 13: From the structure (6) structures (7),(8),(9)and (10) were proposed .Based on (7) the structure of emetine was given. Slide 14: Emetine is found to contain only one C-alkyl group hence structures (9) and (10) are ruled out as they contain 2 alkyl groups. For biogenetic reasons structure (8) is said to be the structure of emetine. SYNTHESIS Openshaw and Whittaker’s Synthesis : SYNTHESIS Openshaw and Whittaker’s Synthesis Slide 19: REFERENCES Organic chemistry of natural products, by,Gurdeep Chatwal , Himalaya Publishing House, page no :- 398 – 407. Slide 20: Thank you You do not have the permission to view this presentation. In order to view it, please contact the author of the presentation.