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Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues

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 salt...

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Main Author: Ramlee, Nurul Izzati
Format: Thesis
Language:English
Published: 2015
Subjects:
RS1-441 Pharmacy and materia medica
Online Access:http://eprints.usm.my/56266/1/00001791934%20NIb.R.pdf
http://eprints.usm.my/56266/
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spelling my.usm.eprints.56266 http://eprints.usm.my/56266/ Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues Ramlee, Nurul Izzati RS1-441 Pharmacy and materia medica 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. 2015-10 Thesis NonPeerReviewed application/pdf en http://eprints.usm.my/56266/1/00001791934%20NIb.R.pdf Ramlee, Nurul Izzati (2015) Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues. Masters thesis, Perpustakaan Hamzah Sendut.
institution Universiti Sains Malaysia
building Hamzah Sendut Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Sains Malaysia
content_source USM Institutional Repository
url_provider http://eprints.usm.my/
language English
topic RS1-441 Pharmacy and materia medica
spellingShingle RS1-441 Pharmacy and materia medica
Ramlee, Nurul Izzati
Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
description 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.
format Thesis
author Ramlee, Nurul Izzati
author_facet Ramlee, Nurul Izzati
author_sort Ramlee, Nurul Izzati
title Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
title_short Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
title_full Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
title_fullStr Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
title_full_unstemmed Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues
title_sort synthesis, characterization and analgesic activity of mitragynine analogues
publishDate 2015
url http://eprints.usm.my/56266/1/00001791934%20NIb.R.pdf
http://eprints.usm.my/56266/
_version_ 1755873160469676032
score 13.211869

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