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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| Format: | Thesis |
| Language: | English |
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2015
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| Online Access: | http://eprints.usm.my/56266/ http://eprints.usm.my/56266/1/00001791934%20NIb.R.pdf |
| _version_ | 1848883306973626368 |
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| author | Ramlee, Nurul Izzati |
| author_facet | Ramlee, Nurul Izzati |
| author_sort | Ramlee, Nurul Izzati |
| building | USM Institutional Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-15T18:48:43Z |
| format | Thesis |
| id | usm-56266 |
| institution | Universiti Sains Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T18:48:43Z |
| publishDate | 2015 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | usm-562662023-01-10T07:20:38Z 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. |
| spellingShingle | RS1-441 Pharmacy and materia medica Ramlee, Nurul Izzati Synthesis, Characterization And Analgesic Activity Of Mitragynine Analogues |
| title | 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_short | Synthesis, Characterization And
Analgesic Activity Of Mitragynine
Analogues |
| title_sort | synthesis, characterization and
analgesic activity of mitragynine
analogues |
| topic | RS1-441 Pharmacy and materia medica |
| url | http://eprints.usm.my/56266/ http://eprints.usm.my/56266/1/00001791934%20NIb.R.pdf |