E22 Kratom and Pseudoindoxyl Metabolites

Guest analysis about kratom pharmacology with academic references for this episode's commentary.  Contact info at end of the show notes if you are seeking help quitting kratom.

 

SOURCES

Angyal, Péter, Kristóf Hegedüs, Bence Balázs Mészáros, János Daru, Ádám Dudás, Anna Rita Galambos, Nariman Essmat, Mahmoud Al-Khrasani, Szilárd Varga, and Tibor Soós. 2023a. “Gram-Scale Syntheses of Kratom Pseudoindoxyl Metabolites: Illuminating the Dynamic Stereochemistry and the Resulting Structural Plasticity of Mitragynine Pseudoindoxyl.” ChemRxiv, February. https://chemrxiv.org/engage/chemrxiv/article-details/63dab15989c04b6693c92cba

Angyal, Péter, Kristóf Hegedüs, Bence Balázs Mészáros, János Daru, Ádám Dudás, Anna Rita Galambos, Nariman Essmat, Mahmoud Al-Khrasani, Szilárd Varga, and Tibor Soós. 2023b. “Total Synthesis and Structural Plasticity of Kratom Pseudoindoxyl Metabolites.” Angewandte Chemie , June, e202303700. https://doi.org/10.1002/anie.202303700

Chakraborty, Soumen, Rajendra Uprety, Amal E. Daibani, Valerie L. Rouzic, Amanda Hunkele, Kevin Appourchaux, Shainnel O. Eans, et al. 2021. “Kratom Alkaloids as Probes for Opioid Receptor Function: Pharmacological Characterization of Minor Indole and Oxindole Alkaloids from Kratom.” ACS Chemical Neuroscience 12 (14): 2661–78. https://doi.org/10.1021/acschemneuro.1c00149

Chakraborty, Soumen, Rajendra Uprety, Samuel T. Slocum, Takeshi Irie, Valerie Le Rouzic, Xiaohai Li, Lisa L. Wilson, et al. 2021. “Oxidative Metabolism as a Modulator of Kratom’s Biological Actions.” Journal of Medicinal Chemistry 64 (22): 16553–72. https://doi.org/10.1021/acs.jmedchem.1c01111 

Ford, Nigel. 2021. “What Is Fermented Kratom?” Kratom.org. October 8, 2021. https://kratom.org/guides/fermented-kratom 

Kamble, Shyam H., Francisco León, Tamara I. King, Erin C. Berthold, Carolina Lopera-Londoño, Kanumuri Siva Rama Raju, Aidan J. Hampson, et al. 2020. “Metabolism of a Kratom Alkaloid Metabolite in Human Plasma Increases Its Opioid Potency and Efficacy.” ACS Pharmacology & Translational Science 3 (6): 1063–68. https://doi.org/10.1021/acsptsci.0c00075

Schaffenburg, William C., Benjamin N. Lockshin, and Cynthia M. C. DeKlotz. 2021. “Polymorphisms: Why Individual Drug Responses Vary.” In Comprehensive Dermatologic Drug Therapy (Fourth Edition), edited by Stephen E. Wolverton, 21–33.e2. Elsevier. https://doi.org/10.1016/B978-0-323-61211-1.00003-6

Takayama, Hiromitsu, Hayato Ishikawa, Mika Kurihara, Mariko Kitajima, Norio Aimi, Dhavadee Ponglux, Fumi Koyama, et al. 2002. “Studies on the Synthesis and Opioid Agonistic Activities of Mitragynine-Related Indole Alkaloids: Discovery of Opioid Agonists Structurally Different from Other Opioid Ligands.” Journal of Medicinal Chemistry 45 (9): 1949–56. https://doi.org/10.1021/jm010576e 

Trescot, Andrea M., Sukdeb Datta, Marion Lee, and Hans Hansen. 2008. “Opioid Pharmacology.” Pain Physician 2008 (11): S133–53. https://www.painphysicianjournal.com/current/pdf?article=OTg3&journal=42

Váradi, András, Gina F. Marrone, Travis C. Palmer, Ankita Narayan, Márton R. Szabó, Valerie Le Rouzic, Steven G. Grinnell, et al. 2016. “Mitragynine/Corynantheidine Pseudoindoxyls As Opioid Analgesics with Mu Agonism and Delta Antagonism, Which Do Not Recruit ß-Arrestin-2.” Journal of Medicinal Chemistry 59 (18): 8381–97. https://doi.org/10.1021/acs.jmedchem.6b00748 

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Zarembo, J. E., B. Douglas, J. Valenta, and J. A. Weisbach. 1974. “Metabolites of Mitragynine.” Journal of Pharmaceutical Sciences 63 (9): 1407–15. https://doi.org/10.1002/jps.2600630916

Zhou, Yuchen, Steven Ramsey, Davide Provasi, Amal El Daibani, Kevin Appourchaux, Soumen Chakraborty, Abhijeet Kapoor, Tao Che, Susruta Majumdar, and Marta Filizola. 2021. “Predicted Mode of Binding to and Allosteric Modulation of the µ-Opioid Receptor by Kratom’s Alkaloids with Reported Antinociception In Vivo.” Biochemistry 60 (18): 1420–29. https://doi.org/10.1021/acs.biochem.0c00658

 

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