Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
| dc.contributor.author | Ramlee, Nurul Izzati | |
| dc.date.accessioned | 2023-01-10T07:16:08Z | |
| dc.date.available | 2023-01-10T07:16:08Z | |
| dc.date.issued | 2015-10 | |
| dc.description.abstract | Mitragyna speciosa contains many alkaloids and mitragynine (MG) is its most abundant alkaloid and has received much attention due to its analgesic property. In this work, a series of MG analogues, which includes 7- hydroxymitragynine (7-0HMG), Na salts of 7-hydroxymitragynine (Na 7-0HMG), K salts of 7-hydroxymitragynine (K 7-0HMG), reduced 7-hydroxymitragynine (reduced 7-0HMG) and nicotinic ester 7-hydroxymitragynine (nicotinic ester 7- OHMG) were synthesized, characterized and evaluated for their analgesic activity. Various oxidants were used to produce 7-0HMG from MG. Oxidation reaction using tert-butyl hydroperoxide (TBHP), hydrogen peroxide (H202) or metachloroperoxybenzoic acid (MCPBA) was carried out in the presence of palladium (Pd) as a catalyst while (bis(trifluoroacetoxy)iodo )benzene (PIFA) was used without any catalyst. H202 was found to be the best oxidant, producing around 99% yield of 7-0HMG, followed by TBHP, MCPBA and PIFA. Na 7-0HMG and K 7-0HMG were synthesized by neutralizing 7-0HMG with sodium hydroxide (NaOH) or potassium hydroxide (KOH) and the best yield was observed when the molar ratio of 7-0HMG: NaOHIKOH at 1: l was used with the yield of 59 and 78% for Na 7- OHMG and K 7-0HMG, respectively. The reduction of 7-0HMG using sodium borohydride (NaBH4) successfully produced reduced 7-0HMG with 99% yield. Whilst, the esterification of nicotinic acid to 7-0HMG in the presence of N,N'Dicyclohexy1carbodiimide (DCC) and 4-Dimethylaminopyridine (DMAP) as a coupling agent and catalyst, respectively has been carried out and produced around 94% yield of nicotinic ester 7-0HMG. | en_US |
| dc.identifier.uri | http://hdl.handle.net/123456789/17127 | |
| dc.language.iso | en | en_US |
| dc.publisher | Universiti Sains Malaysia | en_US |
| dc.subject | Pharmacy | en_US |
| dc.title | Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues | en_US |
| dc.type | Thesis | en_US |
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