One-Pot Conversion of Thebaine to Hydrocodone and Synthesis of Neopinone Ketal

Carroll, Robert J.; Leisch, Hannes; Rochon, Lena; Hudlický, Tomáš; Cox, D. Phillip

doi:10.1021/jo802454v

Cited by 10 publications

(5 citation statements)

References 19 publications

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“…The fabrication of GO-PK was based on a nucleophilic addition reaction of the ketone group. − The typical procedure of functionalized GO-PK is detailed in Supporting Information S2. The fabrication processes of GO-OH and GO-PK are shown in Scheme .…”

Section: Methodsmentioning

confidence: 99%

Preparation of Polyethylene Terephthalate/Polyketone/Graphene Oxide Composite Fibers: Implications for High-Performance Polymer Composites Modified with Carbon Nanomaterials

Gao

Liu

et al. 2021

ACS Appl. Nano Mater.

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Nanocomposite materials with carbon nanotubes and graphene additives have long been considered to be exciting prospective nanomaterials for nanotechnology applications. Some issues of these nanomaterials include poor load transfer, poor interfacial engineering, poor dispersion, and viscosity-related issues, which lead to processing challenges in such nanocomposites, however. Both hydroxylated graphene oxide (GO-OH) and polyketone (PK)-functionalized graphene oxide (GO-PK) were used to improve the properties of polyethylene terephthalate (PET)/PK/graphene oxide (GO) composite fibers. The results showed that there were multiple interactions in the GO-PK. At the molecular level, interactions between PET and PK with GO-PK enhanced their miscibility, and thus, a stable fibril phase structure could be produced following the phase separation. These interactions were demonstrated by various characterization methods. When the fiber with 15 wt % PK/0.1 wt % GO-PK was subjected to 60 min of ultraviolet (UV) treatment, the tensile strength and Young's modulus increased by 37.1 and 77.2% compared with those of 15 wt % PK fibers. This indicated that functionalized graphene oxide has excellent development potential for highperformance nanocomposite fibers.

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Section: Methodsmentioning

confidence: 99%

Preparation of Polyethylene Terephthalate/Polyketone/Graphene Oxide Composite Fibers: Implications for High-Performance Polymer Composites Modified with Carbon Nanomaterials

Gao

Liu

et al. 2021

ACS Appl. Nano Mater.

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“…Thebaine and oripavine are not themselves used therapeutically. However, they are precursors for a wide range of semi-synthetic opioids including, but not limited to, hydrocodone, oxycodone and hydromorphone, as well as naloxone, which is interestingly employed to treat the acute effects of opioid overdose [474][475][476][477][478][479].…”

Section: Papaver Somniferum: Potential Parallels For Future Cannabis mentioning

confidence: 99%

Cannabis sativa: Interdisciplinary Strategies and Avenues for Medical and Commercial Progression Outside of CBD and THC

Oultram

Pegler

Bowser³

et al. 2021

Biomedicines

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Cannabis sativa (Cannabis) is one of the world’s most well-known, yet maligned plant species. However, significant recent research is starting to unveil the potential of Cannabis to produce secondary compounds that may offer a suite of medical benefits, elevating this unique plant species from its illicit narcotic status into a genuine biopharmaceutical. This review summarises the lengthy history of Cannabis and details the molecular pathways that underpin the production of key secondary metabolites that may confer medical efficacy. We also provide an up-to-date summary of the molecular targets and potential of the relatively unknown minor compounds offered by the Cannabis plant. Furthermore, we detail the recent advances in plant science, as well as synthetic biology, and the pharmacology surrounding Cannabis. Given the relative infancy of Cannabis research, we go on to highlight the parallels to previous research conducted in another medically relevant and versatile plant, Papaver somniferum (opium poppy), as an indicator of the possible future direction of Cannabis plant biology. Overall, this review highlights the future directions of cannabis research outside of the medical biology aspects of its well-characterised constituents and explores additional avenues for the potential improvement of the medical potential of the Cannabis plant.

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“…2-9-18 The World Drug Report of 2015 on narcotic drugs states that global opium production reached 7554 tons in 2014 and worldwide consumption is increasing. Because of illicite use, cultivation of the opium poppy continues 4 therefore, it is necessary to find other sources for morphine and codeine [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] The non-narcotic thebaine, the main alkaloid of P. bracteatum, 20 has been a focus of attention because it accumulates thebaine with no morphine and codeine. 21 Thebaine is an excellent starting material for synthesis of diverse morphine agonists and antagonists.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, microbial production of secondary plant metabolites as an alternative method of synthesis of such effective compounds has been of increased interest. [10][11][12][13][14][15][16][17][18] Microbial transformation is the modification of certain compounds by enzymatic reactions 22 to achieve specific and useful metabolite accumulation through environmentally harmless and simpler bioprocesses. 23 Selecting microbial reactions directed toward the native plant hosts as alternative to chemical synthesis employed in traditional methods offers benefits such as quick accumulation of biomass, production of main intermediate molecules separately, simplicity of purification and accessibility of genetic tools for additional optimization.…”

Section: Introductionmentioning

confidence: 99%

Response Surface Methodology Optimization of Thebaine Biotransformation into Codeine and Morphine Using Bacillus sp. FAR

Ataee¹,

Fooladi²,

Namaei³

et al. 2017

IJPER

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Background: Codeine and morphine are important pharmaceuticals having analgesic characteristics. Aim: The current study used response surface methodology to optimize the biotransformation of thebaine into codeine and morphine using Bacillus sp. FAR. Methods: A central composite design was used to determine the optimal concentrations of buffer and thebaine, pH, time, temperature, and biomass. Improvement in transformation was monitored using HPLC-DAD. Results: The optimized conditions employed were pH 7.7 at 36°C for 30 h using a thebaine concentration of 80 µg/mL, 45 mM tris of buffer and 2.9% w/v biomass. The optimal conditions for codeine and morphine production were 2.995 and 1.113 µg, respectively. Conclusion: Optimization demonstrated that pH and biomass had the strongest effects on biotransformation.

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One-Pot Conversion of Thebaine to Hydrocodone and Synthesis of Neopinone Ketal

Cited by 10 publications

References 19 publications

Preparation of Polyethylene Terephthalate/Polyketone/Graphene Oxide Composite Fibers: Implications for High-Performance Polymer Composites Modified with Carbon Nanomaterials

Preparation of Polyethylene Terephthalate/Polyketone/Graphene Oxide Composite Fibers: Implications for High-Performance Polymer Composites Modified with Carbon Nanomaterials

Cannabis sativa: Interdisciplinary Strategies and Avenues for Medical and Commercial Progression Outside of CBD and THC

Response Surface Methodology Optimization of Thebaine Biotransformation into Codeine and Morphine Using Bacillus sp. FAR

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