Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2009, 74, 1179-1193
Published online 2009-08-11 16:51:29

Biotransformations of morphine alkaloids by fungi: N-demethylations, oxidations, and reductions

Vigi Chaudharya, Hannes Leischa, Alena Moudraa, Blake Allena, Vincenzo De Lucaa, D. Phillip Coxb and Tomáš Hudlickýa,*

a Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON L2S 3A1, Canada
b Noramco Inc., 503 Carr Road, Suite 200, Wilmington, DE 19809, USA

Crossref Cited-by Linking

  • de Campos Eduardo G, de Almeida Otávio G G, De Martinis Elaine C P: The role of microorganisms in the biotransformation of psychoactive substances and its forensic relevance: a critical interdisciplinary review. Forensic Sciences Research 2023, 8, 173. <>
  • Zarin Mona Kamelan Zargar, Dehaen Wim, Salehi Peyman, Asl Amir Ata Bahmani: Synthesis and Modification of Morphine and Codeine, Leading to Diverse Libraries with Improved Pain Relief Properties. Pharmaceutics 2023, 15, 1779. <>
  • Firoozi Somayeh, Hosseini-Sarvari Mona: Nanosized CdS as a Reusable Photocatalyst: The Study of Different Reaction Pathways between Tertiary Amines and Aryl Sulfonyl Chlorides through Visible-Light-Induced N-Dealkylation and C–H Activation Processes. J. Org. Chem. 2021, 86, 2117. <>
  • Qaderi Ardeshir, Omidi Mansour, Pour-Aboughadareh Alireza, Poczai Peter, Shaghaghi Javad, Mehrafarin Ali, Ghorbani Nohooji Majid, Etminan Alireza: Molecular diversity and phytochemical variability in the Iranian poppy (Papaver bracteatum Lindl.): A baseline for conservation and utilization in future breeding programmes. Industrial Crops and Products 2019, 130, 237. <>
  • Ataee Nazanin, Fooladi Jamshid, Namaei Mohammad Hasan, Rezadoost Hassan, Mirzajani Fateme: Biocatalysts screening of Papaver bracteatum flora for thebaine transformation to codeine and morphine. Biocatalysis and Agricultural Biotechnology 2017, 9, 127. <>
  • Machara Ales, Endoma‐Arias Mary Ann A., Císařová Ivana, Cox D. Phillip, Hudlicky Tomas: Direct Synthesis of Noroxymorph­one from Thebaine: Unusual CeIV Oxidation of a Methoxydiene‐Iron Complex to an Enone‐γ‐Nitrate. Eur J Org Chem 2016, 2016, 1500. <>
  • Gutmann Bernhard, Elsner Petteri, Cox D. Phillip, Weigl Ulrich, Roberge Dominique M., Kappe C. Oliver: Toward the Synthesis of Noroxymorphone via Aerobic Palladium-Catalyzed Continuous Flow N-Demethylation Strategies. ACS Sustainable Chem. Eng. 2016, 4, 6048. <>
  • Gallagher Ryan, Chebib Mary, Balle Thomas, McLeod Malcolm D.: Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors. Aust. J. Chem. 2015, 68, 1834. <>
  • Hudlicky Tomas: Recent advances in process development for opiate-derived pharmaceutical agents. Can. J. Chem. 2015, 93, 492. <>
  • Endoma‐Arias Mary Ann A., Cox D. Phillip, Hudlicky Tomas: General Method of Synthesis for Naloxone, Naltrexone, Nalbuphone, and Nalbuphine by the Reaction of Grignard Reagents with an Oxazolidine Derived from Oxymorphone. Adv Synth Catal 2013, 355, 1869. <>
  • Joyeau Roger, Planchon Mariane, Abessolo Jenna, Aissa Kevin, Bance Caroline, Buisson Didier: Combinatorial approach to the selection of active microorganisms in biotransformation: Application to sinomenine. Journal of Molecular Catalysis B: Enzymatic 2013, 85-86, 65. <>
  • Machara Ales, Werner Lukas, Endoma‐Arias Mary Ann, Cox D. Phillip, Hudlicky Tomas: Improved Synthesis of Buprenorphine from Thebaine and/or Oripavine via Palladium‐Catalyzed N‐Demethylation/Acylation and/or Concomitant O‐Demethylation. Adv Synth Catal 2012, 354, 613. <>
  • Werner Lukas, Wernerova Martina, Machara Ales, Endoma‐Arias Mary Ann, Duchek Jan, Adams  David R., Cox D. Phillip, Hudlicky Tomas: Unexpected N‐Demethylation of Oxymorphone and Oxycodone N‐Oxides Mediated by the Burgess Reagent: Direct Synthesis of Naltrexone, Naloxone, and Other Antagonists from Oxymorphone. Adv Synth Catal 2012, 354, 2706. <>
  • Machara Ales, Cox D. Phillip, Hudlicky Tomas: Direct Synthesis of Naltrexone by Palladium‐Catalyzed N‐Demethylation/Acylation of Oxymorphone: The Benefit of CH Activation and the Intramolecular Acyl Transfer from C‐14 Hydroxy. Adv Synth Catal 2012, 354, 2713. <>
  • Kok Gaik B., Scammells Peter J.: Improved synthesis of 14-hydroxy opioid pharmaceuticals and intermediates. RSC Adv. 2012, 2, 11318. <>
  • Hudlicky Tomas, Machara Ales, Phillip Cox D.: Synthesis of Nalbuphine from Oripavine via N-Demethylation of N-Cyclobutylmethyl Oripavine. Heterocycle 2012, 84, 615. <>
  • Kok Gaik B., Scammells Peter J.: Further investigations into the N-demethylation of oripavine using iron and stainless steel. Org. Biomol. Chem. 2011, 9, 1008. <>
  • Kok Gaik B., Scammells Peter J.: N-Demethylation of N-methyl alkaloids with ferrocene. Bioorganic & Medicinal Chemistry Letters 2010, 20, 4499. <>
  • Kok Gaik B., Pye Cory C., Singer Robert D., Scammells Peter J.: Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids. J. Org. Chem. 2010, 75, 4806. <>