Mitragynine (BioDeep_00000000647)

   

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(.ALPHA.E,2S,3S,12.BETA.S)-3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER

化学式: C23H30N2O4 (398.220546)
中文名称: 帽柱木碱盐酸盐
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 7.95%

分子结构信息

SMILES: CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=C3C(=CC=C4)OC
InChI: InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+/m1/s1

描述信息

Mitragynine itself acts primarily via -opioid receptors, although its oxidation product mitragynine-pseudoindoxyl, which is likely to be a major component of kratom that has been aged or stored for extended periods, acts as a fairly selective -opioid agonist with little affinity for receptors. Another alkaloid with a major contribution to the opioid activity of the kratom plant is the related compound 7-hydroxymitragynine, which while present in the plant in much smaller quantities than mitragynine, is a much more potent opioid agonist.
Mitragynine is a monoterpenoid indole alkaloid.
Mitragynine is a natural product found in Mitragyna speciosa with data available.

同义名列表

27 个代谢物同义名

(.ALPHA.E,2S,3S,12.BETA.S)-3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER; INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3S,12BS)-; methyl (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate; Methyl (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0,.0,]heptadeca-1(10),11(16),12,14-tetraen-4-yl]-3-methoxyprop-2-enoic acid; methyl (2E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate; methyl(e)-2-[(2s,3s,12bs)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate; (E)-Methyl 2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate; 16,17-didehydro-9,17-dimethoxy-17,18-seco-20-alpha-yohimban-16-carboxylic acid methyl ester; mitragynine, (3beta,16E,20beta)-isomer; Mitragynine, 0.1mg/ml in Methanol; mitragynine, (3beta,16E)-isomer; Mitragynine, 1mg/ml in Methanol; mitragynine ethanedisulfonate; mitragynine monohydrochloride; mitragynine, (16E)-isomer; 9-Methoxycorynantheidine; MITRAGYNINE [WHO-DD]; MITRAGYNINE PICRATE; Mitragynine - 95\\%; Mitragynine [MI]; kratom alkaloids; (-)-Mitragynine; SK And F-12711; SK And F 12711; Mitragynine; Mitragynin; Mitragynine



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

26 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Alice Ameline, Laurie Gheddar, Nadia Arbouche, Adeline Blanchot, Jean-Sebastien Raul, Pascal Kintz. Testing for Kratom alkaloids in fingernail clippings - not only mitragynine. Journal of pharmaceutical and biomedical analysis. 2024 Jun; 243(?):116078. doi: 10.1016/j.jpba.2024.116078. [PMID: 38489958]
  • Marilyn A Huestis, Martin A Brett, John Bothmer, Ramsey Atallah. Human Mitragynine and 7-Hydroxymitragynine Pharmacokinetics after Single and Multiple Daily Doses of Oral Encapsulated Dried Kratom Leaf Powder. Molecules (Basel, Switzerland). 2024 Feb; 29(5):. doi: 10.3390/molecules29050984. [PMID: 38474495]
  • Philip W Melchert, Qingchen Zhang, Sushobhan Mukhopadhyay, Siva Rama Raju Kanumuri, Christopher R McCurdy, John S Markowitz. An in vitro evaluation of kratom (Mitragyna speciosa) on the catalytic activity of carboxylesterase 1 (CES1). Chemico-biological interactions. 2023 Sep; ?(?):110715. doi: 10.1016/j.cbi.2023.110715. [PMID: 37716419]
  • Rima Atria Japarin, Norsyifa Harun, Zurina Hassan, Christian P Müller. The dopamine D1 receptor antagonist SCH-23390 blocks the acquisition, but not expression of mitragynine-induced conditioned place preference in rats. Behavioural brain research. 2023 Aug; 453(?):114638. doi: 10.1016/j.bbr.2023.114638. [PMID: 37619769]
  • Yinan Wu, Chang Liu, Anna Koganitsky, Franklin Gong, Sijin Li. Discovering Dynamic Plant Enzyme Complexes in Yeast for Kratom Alkaloid Pathway Identification. Angewandte Chemie (International ed. in English). 2023 Aug; ?(?):e202307995. doi: 10.1002/anie.202307995. [PMID: 37549372]
  • Daniel J Farkas, Saadet Inan, Laila N Heydari, Clare T Johnson, Pingwei Zhao, Heather B Bradshaw, Sara Jane Ward, Scott M Rawls. Cannabinoid mechanisms contribute to the therapeutic efficacy of the kratom alkaloid mitragynine against neuropathic, but not inflammatory pain. Life sciences. 2023 Jun; 328(?):121878. doi: 10.1016/j.lfs.2023.121878. [PMID: 37392779]
  • Carsten Schotte, Yindi Jiang, Dagny Grzech, Thu-Thuy T Dang, Larissa C Laforest, Francisco León, Marco Mottinelli, Satya Swathi Nadakuduti, Christopher R McCurdy, Sarah E O'Connor. Directed Biosynthesis of Mitragynine Stereoisomers. Journal of the American Chemical Society. 2023 Mar; 145(9):4957-4963. doi: 10.1021/jacs.2c13644. [PMID: 36883326]
  • Mohamad Azmeer Effendy, Suleiman Yunusa, Noorul Hamizah Mat, Ahmad Tarmizi Che Has, Christian P Müller, Zurina Hassan. The role of AMPA and NMDA receptors in mitragynine effects on hippocampal synaptic plasticity. Behavioural brain research. 2023 02; 438(?):114169. doi: 10.1016/j.bbr.2022.114169. [PMID: 36273648]
  • Anders Helander, Alexia Rylski. Drug testing for mitragynine and kratom: Analytical challenges and medico-legal considerations. Drug testing and analysis. 2023 Feb; 15(2):213-219. doi: 10.1002/dta.3391. [PMID: 36258649]
  • Kirsten Elin Smith, Abhisheak Sharma, Oliver Grundmann, Christopher R McCurdy. Kratom Alkaloids: A Blueprint?. ACS chemical neuroscience. 2023 01; 14(2):195-197. doi: 10.1021/acschemneuro.2c00704. [PMID: 36594896]
  • Rima Atria Japarin, Norsyifa Harun, Zurina Hassan, Mohammed Shoaib. Mitragynine, a primary constituent of kratom reinstates morphine-seeking behaviour in rats. Behavioural pharmacology. 2022 Dec; ?(?):. doi: 10.1097/fbp.0000000000000715. [PMID: 36752325]
  • Jack E Henningfield, Joseph V Rodricks, Aaron M Magnuson, Marilyn A Huestis. Respiratory effects of oral mitragynine and oxycodone in a rodent model. Psychopharmacology. 2022 Dec; 239(12):3793-3804. doi: 10.1007/s00213-022-06244-z. [PMID: 36308562]
  • Radhiahtul Raehan Mustafa, Rashidah Sukor, Siti Mariam Mohd Nor, Nazamid Saari. Methyl ester and aromatic ether modification of mitragynine for generation of mitragynine-specific polyclonal antibodies. Journal of immunological methods. 2022 Aug; 507(?):113291. doi: 10.1016/j.jim.2022.113291. [PMID: 35640723]
  • Yee Shan Sim, Zan Yang Chong, Juzaili Azizi, Choon Fu Goh. Development and validation of a gradient HPLC-UV method for mitragynine following in vitro skin permeation studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2022 Jul; 1204(?):123316. doi: 10.1016/j.jchromb.2022.123316. [PMID: 35700649]
  • George S Behonick, Christina Vu, Larry Czarnecki, Maisie El-Ters, Kevin G Shanks. Two Single-Drug Fatal Intoxications by Mitragynine. Journal of analytical toxicology. 2022 May; 46(5):e110-e114. doi: 10.1093/jat/bkac016. [PMID: 35285475]
  • Bianka Várnai, Ferenc Zsila, Zoltán Szakács, Zsófia Garádi, Milo Malanga, Szabolcs Béni. Sulfobutylation of Beta-Cyclodextrin Enhances the Complex Formation with Mitragynine: An NMR and Chiroptical Study. International journal of molecular sciences. 2022 Mar; 23(7):. doi: 10.3390/ijms23073844. [PMID: 35409208]
  • Norsyifa Harun, Nur Azzalia Kamaruzaman, Zarif Mohamed Sofian, Zurina Hassan. Mini review: Potential therapeutic values of mitragynine as an opioid substitution therapy. Neuroscience letters. 2022 03; 773(?):136500. doi: 10.1016/j.neulet.2022.136500. [PMID: 35114335]
  • Kai Yue, Jonathan L Katz, Xiji Shu. Physiological dependence to mitragynine indicated by a rapid cross-dependence procedure with heroin-dependent mice. Psychopharmacology. 2022 Mar; 239(3):897-908. doi: 10.1007/s00213-022-06080-1. [PMID: 35107609]
  • Nurul H M Yusoff, Zurina Hassan, Vikneswaran Murugaiyah, Christian P Müller. The effect of mitragynine on extracellular activity of brain dopamine and its metabolites. Brain research bulletin. 2022 01; 178(?):1-8. doi: 10.1016/j.brainresbull.2021.11.002. [PMID: 34774992]
  • Soumen Chakraborty, Rajendra Uprety, Samuel T Slocum, Takeshi Irie, Valerie Le Rouzic, Xiaohai Li, Lisa L Wilson, Brittany Scouller, Amy F Alder, Andrew C Kruegel, Michael Ansonoff, Andras Varadi, Shainnel O Eans, Amanda Hunkele, Abdullah Allaoa, Sanjay Kalra, Jin Xu, Ying Xian Pan, John Pintar, Bronwyn M Kivell, Gavril W Pasternak, Michael D Cameron, Jay P McLaughlin, Dalibor Sames, Susruta Majumdar. Oxidative Metabolism as a Modulator of Kratom's Biological Actions. Journal of medicinal chemistry. 2021 11; 64(22):16553-16572. doi: 10.1021/acs.jmedchem.1c01111. [PMID: 34783240]
  • Illa S Johari, Norsyifa Harun, Zarif M Sofian, Mohammed Shoaib. Pentylenetetrazol-like stimulus is not produced following naloxone-precipitated mitragynine withdrawal in rats. Psychopharmacology. 2021 Nov; 238(11):3183-3191. doi: 10.1007/s00213-021-05934-4. [PMID: 34333672]
  • Mohamad Azmeer Effendy, Suleiman Yunusa, Zainiharyati M Zain, Zurina Hassan. Real time monitoring of dopamine release evoked by mitragynine (Kratom): An insight through electrochemical sensor. Neuroscience letters. 2021 10; 763(?):136183. doi: 10.1016/j.neulet.2021.136183. [PMID: 34418508]
  • Soumen Chakraborty, Jeffrey F DiBerto, Abdelfattah Faouzi, Sarah M Bernhard, Anna M Gutridge, Steven Ramsey, Yuchen Zhou, Davide Provasi, Nitin Nuthikattu, Rahul Jilakara, Melissa N F Nelson, Wesley B Asher, Shainnel O Eans, Lisa L Wilson, Satyanarayana M Chintala, Marta Filizola, Richard M van Rijn, Elyssa B Margolis, Bryan L Roth, Jay P McLaughlin, Tao Che, Dalibor Sames, Jonathan A Javitch, Susruta Majumdar. A Novel Mitragynine Analog with Low-Efficacy Mu Opioid Receptor Agonism Displays Antinociception with Attenuated Adverse Effects. Journal of medicinal chemistry. 2021 09; 64(18):13873-13892. doi: 10.1021/acs.jmedchem.1c01273. [PMID: 34505767]
  • Amadeo Pesce, Raymond Sundyhanata, Dennis Ritz, Richard Thomas, Gregory Ackerman, Katie Bollman. Effects of a Pandemic and Isolation on Alcohol and Psychoactive Medication Use in a Population of Rehabilitation and Pain Patients. Annals of clinical and laboratory science. 2021 Sep; 51(5):694-697. doi: . [PMID: 34686512]
  • Sarah E Voelker, Sara E Kern, Travis M Falconer, Michael D Thatcher, David M Skelton, Kirk W Gaston, Adam C Lanzarotta, Lisa M Lorenz, JaCinta S Batson, Jonathan J Litzau. Evaluation of four field portable devices for the rapid detection of mitragynine in suspected kratom products. Journal of pharmaceutical and biomedical analysis. 2021 Jul; 201(?):114104. doi: 10.1016/j.jpba.2021.114104. [PMID: 33964724]
  • Rahimah Hassan, Nurulhasanah Othman, Sharif M Mansor, Christian P Müller, Zurina Hassan. Proteomic analysis reveals brain Rab35 as a potential biomarker of mitragynine withdrawal in rats. Brain research bulletin. 2021 07; 172(?):139-150. doi: 10.1016/j.brainresbull.2021.04.018. [PMID: 33901587]
  • Yong Sean Goh, Thiruventhan Karunakaran, Vikneswaran Murugaiyah, Rameshkumar Santhanam, Mohamad Hafizi Abu Bakar, Surash Ramanathan. Accelerated Solvent Extractions (ASE) of Mitragyna speciosa Korth. (Kratom) Leaves: Evaluation of Its Cytotoxicity and Antinociceptive Activity. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123704. [PMID: 34204457]
  • Shyam H Kamble, Erin C Berthold, Tamara I King, Siva Rama Raju Kanumuri, Raluca Popa, Julius R Herting, Francisco León, Abhisheak Sharma, Lance R McMahon, Bonnie A Avery, Christopher R McCurdy. Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. Journal of natural products. 2021 04; 84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. [PMID: 33620222]
  • Nelson Jeng-Yeou Chear, Francisco León, Abhisheak Sharma, Siva Rama Raju Kanumuri, Grant Zwolinski, Khalil A Abboud, Darshan Singh, Luis F Restrepo, Avi Patel, Takato Hiranita, Surash Ramanathan, Aidan J Hampson, Lance R McMahon, Christopher R McCurdy. Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors. Journal of natural products. 2021 04; 84(4):1034-1043. doi: 10.1021/acs.jnatprod.0c01055. [PMID: 33635670]
  • Kimheang Ya, Janthima Methaneethorn, Quoc Ba Tran, Satariya Trakulsrichai, Winai Wananukul, Manupat Lohitnavy. Development of a Physiologically Based Pharmacokinetic Model of Mitragynine, Psychoactive Alkaloid in Kratom (Mitragyna Speciosa Korth.), In Rats and Humans. Journal of psychoactive drugs. 2021 Apr; 53(2):127-139. doi: 10.1080/02791072.2020.1849877. [PMID: 34003732]
  • Farah Wahida Suhaimi, Zurina Hassan, Sharif Mahsufi Mansor, Christian P Müller. The effects of chronic mitragynine (Kratom) exposure on the EEG in rats. Neuroscience letters. 2021 02; 745(?):135632. doi: 10.1016/j.neulet.2021.135632. [PMID: 33444671]
  • Erin C Berthold, Shyam H Kamble, Kanumuri S Raju, Tamara I King, Raluca Popa, Abhisheak Sharma, Francisco León, Bonnie A Avery, Lance R McMahon, Christopher R McCurdy. Preclinical pharmacokinetic study of speciociliatine, a kratom alkaloid, in rats using an UPLC-MS/MS method. Journal of pharmaceutical and biomedical analysis. 2021 Feb; 194(?):113778. doi: 10.1016/j.jpba.2020.113778. [PMID: 33277117]
  • Rima Atria Japarin, Nurul Hasnida Yusoff, Zurina Hassan, Christian P Müller, Norsyifa Harun. Cross-reinstatement of mitragynine and morphine place preference in rats. Behavioural brain research. 2021 02; 399(?):113021. doi: 10.1016/j.bbr.2020.113021. [PMID: 33227244]
  • Rakshit S Tanna, Dan-Dan Tian, Nadja B Cech, Nicholas H Oberlies, Allan E Rettie, Kenneth E Thummel, Mary F Paine. Refined Prediction of Pharmacokinetic Kratom-Drug Interactions: Time-Dependent Inhibition Considerations. The Journal of pharmacology and experimental therapeutics. 2021 01; 376(1):64-73. doi: 10.1124/jpet.120.000270. [PMID: 33093187]
  • D A Todd, J J Kellogg, E D Wallace, M Khin, L Flores-Bocanegra, R S Tanna, S McIntosh, H A Raja, T N Graf, S E Hemby, M F Paine, N H Oberlies, N B Cech. Chemical composition and biological effects of kratom (Mitragyna speciosa): In vitro studies with implications for efficacy and drug interactions. Scientific reports. 2020 11; 10(1):19158. doi: 10.1038/s41598-020-76119-w. [PMID: 33154449]
  • Elizabeth A Maxwell, Tamara I King, Shyam H Kamble, Kanumuri Siva Rama Raju, Erin C Berthold, Francisco León, Bonnie A Avery, Lance R McMahon, Christopher R McCurdy, Abhisheak Sharma. Pharmacokinetics and Safety of Mitragynine in Beagle Dogs. Planta medica. 2020 Nov; 86(17):1278-1285. doi: 10.1055/a-1212-5475. [PMID: 32693425]
  • Azin Behnood-Rod, Ranjithkumar Chellian, Ryann Wilson, Takato Hiranita, Abhisheak Sharma, Francisco Leon, Christopher R McCurdy, Lance R McMahon, Adriaan W Bruijnzeel. Evaluation of the rewarding effects of mitragynine and 7-hydroxymitragynine in an intracranial self-stimulation procedure in male and female rats. Drug and alcohol dependence. 2020 10; 215(?):108235. doi: 10.1016/j.drugalcdep.2020.108235. [PMID: 32889450]
  • Walter C Prozialeck, Joshua R Edwards, Peter C Lamar, Balbina J Plotkin, Ira M Sigar, Oliver Grundmann, Charles A Veltri. Evaluation of the Mitragynine Content, Levels of Toxic Metals and the Presence of Microbes in Kratom Products Purchased in the Western Suburbs of Chicago. International journal of environmental research and public health. 2020 07; 17(15):. doi: 10.3390/ijerph17155512. [PMID: 32751712]
  • Surash Ramanathan, Christopher R McCurdy. Kratom (Mitragyna speciosa): worldwide issues. Current opinion in psychiatry. 2020 07; 33(4):312-318. doi: 10.1097/yco.0000000000000621. [PMID: 32452943]
  • Michelle R Peace, Mika E Smith, Justin L Poklis. The analysis of commercially available natural products recommended for use in electronic cigarettes. Rapid communications in mass spectrometry : RCM. 2020 Jun; 34(11):e8771. doi: 10.1002/rcm.8771. [PMID: 32110843]
  • Mei Jin Lee, Surash Ramanathan, Sharif Mahsufi Mansor, Soo Choon Tan. Development of an ELISA for detection of mitragynine and its metabolites in human urine. Analytical biochemistry. 2020 06; 599(?):113733. doi: 10.1016/j.ab.2020.113733. [PMID: 32302607]
  • Lindsay E Johnson, Lilian Balyan, Amy Magdalany, Fizza Saeed, Robert Salinas, Starla Wallace, Charles A Veltri, Marc T Swogger, Zach Walsh, Oliver Grundmann. The Potential for Kratom as an Antidepressant and Antipsychotic. The Yale journal of biology and medicine. 2020 06; 93(2):283-289. doi: . [PMID: 32607089]
  • Stephanie Basiliere, Sarah Kerrigan. CYP450-Mediated Metabolism of Mitragynine and Investigation of Metabolites in Human Urine. Journal of analytical toxicology. 2020 May; 44(4):301-313. doi: 10.1093/jat/bkz108. [PMID: 32008041]
  • Stephanie Basiliere, Sarah Kerrigan. Temperature and pH-Dependent Stability of Mitragyna Alkaloids. Journal of analytical toxicology. 2020 May; 44(4):314-324. doi: 10.1093/jat/bkz103. [PMID: 31897484]
  • Jeffery D Foss, Sunil U Nayak, Christopher S Tallarida, Daniel J Farkas, Sara J Ward, Scott M Rawls. Mitragynine, bioactive alkaloid of kratom, reduces chemotherapy-induced neuropathic pain in rats through α-adrenoceptor mechanism. Drug and alcohol dependence. 2020 04; 209(?):107946. doi: 10.1016/j.drugalcdep.2020.107946. [PMID: 32145665]
  • Anna M Gutridge, Meridith T Robins, Robert J Cassell, Rajendra Uprety, Kendall L Mores, Mee Jung Ko, Gavril W Pasternak, Susruta Majumdar, Richard M van Rijn. G protein-biased kratom-alkaloids and synthetic carfentanil-amide opioids as potential treatments for alcohol use disorder. British journal of pharmacology. 2020 04; 177(7):1497-1513. doi: 10.1111/bph.14913. [PMID: 31705528]
  • Stephanie Basiliere, Sarah Kerrigan. Identification of metabolites and potential biomarkers of kratom in urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Mar; 1140(?):121971. doi: 10.1016/j.jchromb.2020.121971. [PMID: 32058315]
  • Darshan Singh, Nelson Jeng Yeou Chear, Suresh Narayanan, Francisco Leon, Abhisheak Sharma, Christopher R McCurdy, Bonnie A Avery, Vicknasingam Balasingam. Patterns and reasons for kratom (Mitragyna speciosa) use among current and former opioid poly-drug users. Journal of ethnopharmacology. 2020 Mar; 249(?):112462. doi: 10.1016/j.jep.2019.112462. [PMID: 31816368]
  • Jonathan Schimmel, Richard C Dart. Kratom (Mitragyna Speciosa) Liver Injury: A Comprehensive Review. Drugs. 2020 Feb; 80(3):263-283. doi: 10.1007/s40265-019-01242-6. [PMID: 31919755]
  • Changho Han, Joza Schmitt, Kristen M Gilliland. DARK Classics in Chemical Neuroscience: Kratom. ACS chemical neuroscience. 2020 Jan; ?(?):. doi: 10.1021/acschemneuro.9b00535. [PMID: 31841631]
  • Samuel Obeng, Shyam H Kamble, Morgan E Reeves, Luis F Restrepo, Avi Patel, Mira Behnke, Nelson J-Y Chear, Surash Ramanathan, Abhisheak Sharma, Francisco León, Takato Hiranita, Bonnie A Avery, Lance R McMahon, Christopher R McCurdy. Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids. Journal of medicinal chemistry. 2020 01; 63(1):433-439. doi: 10.1021/acs.jmedchem.9b01465. [PMID: 31834797]
  • Nicholas Nacca, Rachel F Schult, Lingyun Li, David C Spink, Gary Ginsberg, Kristen Navarette, Jeanna Marraffa. Kratom Adulterated with Phenylethylamine and Associated Intracerebral Hemorrhage: Linking Toxicologists and Public Health Officials to Identify Dangerous Adulterants. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2020 01; 16(1):71-74. doi: 10.1007/s13181-019-00741-y. [PMID: 31713176]
  • Jun Ogata, Maiko Kawamura, Takashi Hakamatsuka, Ruri Kikura-Hanajiri. [Discrimination of Kratom Products by an Improved PCR-RFLP Method]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2020; 140(12):1501-1508. doi: 10.1248/yakushi.20-00170. [PMID: 33268690]
  • Yea Lu Tay, Azimah Amanah, Mohd Ilham Adenan, Habibah Abdul Wahab, Mei Lan Tan. Mitragynine, an euphoric compound inhibits hERG1a/1b channel current and upregulates the complexation of hERG1a-Hsp90 in HEK293-hERG1a/1b cells. Scientific reports. 2019 12; 9(1):19757. doi: 10.1038/s41598-019-56106-6. [PMID: 31874991]
  • Shyam H Kamble, Abhisheak Sharma, Tamara I King, Francisco León, Christopher R McCurdy, Bonnie A Avery. Metabolite profiling and identification of enzymes responsible for the metabolism of mitragynine, the major alkaloid of Mitragyna speciosa (kratom). Xenobiotica; the fate of foreign compounds in biological systems. 2019 Nov; 49(11):1279-1288. doi: 10.1080/00498254.2018.1552819. [PMID: 30547698]
  • Dinesh Sangarran Ramachandram, Thenmoly Damodaran, Hadzliana Zainal, Vikneswaran Murugaiyah, Surash Ramanathan. Pharmacokinetics and pharmacodynamics of mitragynine, the principle alkaloid of Mitragyna speciosa: present knowledge and future directions in perspective of pain. Journal of basic and clinical physiology and pharmacology. 2019 Oct; 31(1):. doi: 10.1515/jbcpp-2019-0138. [PMID: 31665120]
  • Siti R Yusof, Mahathir Mohd Uzid, Eng-Huat Teh, Nur Aziah Hanapi, Mazlin Mohideen, Ahmad Saifuddin Mohamad Arshad, Mohd Nizam Mordi, Irena Loryan, Margareta Hammarlund-Udenaes. Rate and extent of mitragynine and 7-hydroxymitragynine blood-brain barrier transport and their intra-brain distribution: the missing link in pharmacodynamic studies. Addiction biology. 2019 09; 24(5):935-945. doi: 10.1111/adb.12661. [PMID: 30088322]
  • John M Corkery, Peter Streete, Hugh Claridge, Christine Goodair, Duccio Papanti, Laura Orsolini, Fabrizio Schifano, Kanav Sikka, Sophie Körber, Amy Hendricks. Characteristics of deaths associated with kratom use. Journal of psychopharmacology (Oxford, England). 2019 09; 33(9):1102-1123. doi: 10.1177/0269881119862530. [PMID: 31429622]
  • Scott E Hemby, Scot McIntosh, Francisco Leon, Stephen J Cutler, Christopher R McCurdy. Abuse liability and therapeutic potential of the Mitragyna speciosa (kratom) alkaloids mitragynine and 7-hydroxymitragynine. Addiction biology. 2019 09; 24(5):874-885. doi: 10.1111/adb.12639. [PMID: 29949228]
  • Walter C Prozialeck, Bonnie A Avery, Edward W Boyer, Oliver Grundmann, Jack E Henningfield, Andrew C Kruegel, Lance R McMahon, Christopher R McCurdy, Marc T Swogger, Charles A Veltri, Darshan Singh. Kratom policy: The challenge of balancing therapeutic potential with public safety. The International journal on drug policy. 2019 08; 70(?):70-77. doi: 10.1016/j.drugpo.2019.05.003. [PMID: 31103778]
  • Zurina Hassan, Farah W Suhaimi, Surash Ramanathan, King-Hwa Ling, Mohamad A Effendy, Christian P Müller, Hans C Dringenberg. Mitragynine (Kratom) impairs spatial learning and hippocampal synaptic transmission in rats. Journal of psychopharmacology (Oxford, England). 2019 07; 33(7):908-918. doi: 10.1177/0269881119844186. [PMID: 31081443]
  • Kimheang Ya, Wimonchat Tangamornsuksan, C Norman Scholfield, Janthima Methaneethorn, Manupat Lohitnavy. Pharmacokinetics of mitragynine, a major analgesic alkaloid in kratom (Mitragyna speciosa): A systematic review. Asian journal of psychiatry. 2019 Jun; 43(?):73-82. doi: 10.1016/j.ajp.2019.05.016. [PMID: 31100603]
  • Kristen L Fowble, Rabi A Musah. A validated method for the quantification of mitragynine in sixteen commercially available Kratom (Mitragyna speciosa) products. Forensic science international. 2019 Jun; 299(?):195-202. doi: 10.1016/j.forsciint.2019.04.009. [PMID: 31059866]
  • Noradliyanti Rusli, Azimah Amanah, Gurjeet Kaur, Mohd Ilham Adenan, Shaida Fariza Sulaiman, Habibah Abdul Wahab, Mei Lan Tan. The inhibitory effects of mitragynine on P-glycoprotein in vitro. Naunyn-Schmiedeberg's archives of pharmacology. 2019 04; 392(4):481-496. doi: 10.1007/s00210-018-01605-y. [PMID: 30604191]
  • Rhome L Hughes. Fatal combination of mitragynine and quetiapine - a case report with discussion of a potential herb-drug interaction. Forensic science, medicine, and pathology. 2019 03; 15(1):110-113. doi: 10.1007/s12024-018-0049-9. [PMID: 30498933]
  • Bonnie A Avery, Sai P Boddu, Abhisheak Sharma, Edward B Furr, Francisco Leon, Stephen J Cutler, Christopher R McCurdy. Comparative Pharmacokinetics of Mitragynine after Oral Administration of Mitragyna speciosa (Kratom) Leaf Extracts in Rats. Planta medica. 2019 Mar; 85(4):340-346. doi: 10.1055/a-0770-3683. [PMID: 30452072]
  • Lauren C Smith, Lucy Lin, Candy S Hwang, Bin Zhou, Diane M Kubitz, Huiying Wang, Kim D Janda. Lateral Flow Assessment and Unanticipated Toxicity of Kratom. Chemical research in toxicology. 2019 01; 32(1):113-121. doi: 10.1021/acs.chemrestox.8b00218. [PMID: 30380840]
  • ". Determination of Alkaloids in Mitragyna speciosa (Kratom) Raw Materials and Dietary Supplements by HPLC-UV: Single-Laboratory Validation, First Action 2017.14. Journal of AOAC International. 2019 Jan; 102(1):322-324. doi: 10.1093/jaoac/102.1.322. [PMID: 30594274]
  • Kai Yue, Theresa A Kopajtic, Jonathan L Katz. Abuse liability of mitragynine assessed with a self-administration procedure in rats. Psychopharmacology. 2018 Oct; 235(10):2823-2829. doi: 10.1007/s00213-018-4974-9. [PMID: 30039246]
  • Lea Wagmann, Hans H Maurer, Markus R Meyer. Inhibition and stimulation of the human breast cancer resistance protein as in vitro predictor of drug-drug interactions of drugs of abuse. Archives of toxicology. 2018 09; 92(9):2875-2884. doi: 10.1007/s00204-018-2276-y. [PMID: 30083819]
  • R B Raffa, J V Pergolizzi, R Taylor, M H Ossipov. Nature's first 'atypical opioids': Kratom and mitragynines. Journal of clinical pharmacy and therapeutics. 2018 Jun; 43(3):437-441. doi: 10.1111/jcpt.12676. [PMID: 29520812]
  • Nurul H M Yusoff, Sharif M Mansor, Christian P Müller, Zurina Hassan. Baclofen blocks the acquisition and expression of mitragynine-induced conditioned place preference in rats. Behavioural brain research. 2018 06; 345(?):65-71. doi: 10.1016/j.bbr.2018.02.039. [PMID: 29499286]
  • Andrew C Kruegel, Oliver Grundmann. The medicinal chemistry and neuropharmacology of kratom: A preliminary discussion of a promising medicinal plant and analysis of its potential for abuse. Neuropharmacology. 2018 05; 134(Pt A):108-120. doi: 10.1016/j.neuropharm.2017.08.026. [PMID: 28830758]
  • Stephanie Basiliere, Kelsie Bryand, Sarah Kerrigan. Identification of five Mitragyna alkaloids in urine using liquid chromatography-quadrupole/time of flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Mar; 1080(?):11-19. doi: 10.1016/j.jchromb.2018.02.010. [PMID: 29459087]
  • Darshan Singh, Christian P Müller, Vikneswaran Murugaiyah, Shahrul Bariyah Sahul Hamid, Balasingam K Vicknasingam, Bonnie Avery, Nelson Jeng Yeou Chear, Sharif Mahsufi Mansor. Evaluating the hematological and clinical-chemistry parameters of kratom (Mitragyna speciosa) users in Malaysia. Journal of ethnopharmacology. 2018 Mar; 214(?):197-206. doi: 10.1016/j.jep.2017.12.017. [PMID: 29248450]
  • Mei Jin Lee, Surash Ramanathan, Sharif Mahsufi Mansor, Keng Yoon Yeong, Soo Choon Tan. Method validation in quantitative analysis of phase I and phase II metabolites of mitragynine in human urine using liquid chromatography-tandem mass spectrometry. Analytical biochemistry. 2018 02; 543(?):146-161. doi: 10.1016/j.ab.2017.12.021. [PMID: 29248503]
  • Marc T Swogger, Zach Walsh. Kratom use and mental health: A systematic review. Drug and alcohol dependence. 2018 02; 183(?):134-140. doi: 10.1016/j.drugalcdep.2017.10.012. [PMID: 29248691]
  • Loren Tapp, Jessica G Ramsey, Anita Wen, Roy Gerona. Synthetic Cannabinoid and Mitragynine Exposure of Law Enforcement Agents During the Raid of an Illegal Laboratory - Nevada, 2014. MMWR. Morbidity and mortality weekly report. 2017 Dec; 66(47):1291-1294. doi: 10.15585/mmwr.mm6647a3. [PMID: 29190268]
  • Dania Cheaha, Chayaporn Reakkamnuan, Jakkrit Nukitram, Somsmorn Chittrakarn, Pimpimol Phukpattaranont, Niwat Keawpradub, Ekkasit Kumarnsit. Effects of alkaloid-rich extract from Mitragyna speciosa (Korth.) Havil. on naloxone-precipitated morphine withdrawal symptoms and local field potential in the nucleus accumbens of mice. Journal of ethnopharmacology. 2017 Aug; 208(?):129-137. doi: 10.1016/j.jep.2017.07.008. [PMID: 28687506]
  • Nurul H M Yusoff, Sharif M Mansor, Christian P Müller, Zurina Hassan. Opioid receptors mediate the acquisition, but not the expression of mitragynine-induced conditioned place preference in rats. Behavioural brain research. 2017 08; 332(?):1-6. doi: 10.1016/j.bbr.2017.05.059. [PMID: 28559179]
  • Darshan Singh, Suresh Narayanan, Balasingam Vicknasingam, Ornella Corazza, Rita Santacroce, Andres Roman-Urrestarazu. Changing trends in the use of kratom (Mitragyna speciosa) in Southeast Asia. Human psychopharmacology. 2017 05; 32(3):. doi: 10.1002/hup.2582. [PMID: 28544011]
  • Olwen Domingo, Gabriele Roider, Andreas Stöver, Matthias Graw, Frank Musshoff, Hans Sachs, Wolfgang Bicker. Mitragynine concentrations in two fatalities. Forensic science international. 2017 Feb; 271(?):e1-e7. doi: 10.1016/j.forsciint.2016.12.020. [PMID: 28089300]
  • Toshiyuki Matsunaga, Yoshifumi Morikawa, Kyoko Kamase, Misato Horinouchi, Yasuhide Sasajima, Koichi Suenami, Kiyohito Sato, Yuji Takekoshi, Satoshi Endo, Ossama El-Kabbani, Akira Ikari. Enhancement of Endothelial Barrier Permeability by Mitragynine. Biological & pharmaceutical bulletin. 2017; 40(10):1779-1783. doi: 10.1248/bpb.b17-00117. [PMID: 28966251]
  • Wai Mun Kong, Zamri Chik, Zahurin Mohamed, Mohammed A Alshawsh. Physicochemical Characterization of Mitragyna speciosa Alkaloid Extract and Mitragynine using In Vitro High Throughput Assays. Combinatorial chemistry & high throughput screening. 2017; 20(9):796-803. doi: 10.2174/1386207320666171026121820. [PMID: 29076424]
  • Alicia G Lydecker, Abhisheak Sharma, Christopher R McCurdy, Bonnie A Avery, Kavita M Babu, Edward W Boyer. Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2016 12; 12(4):341-349. doi: 10.1007/s13181-016-0588-y. [PMID: 27752985]
  • Walter C Prozialeck. Update on the Pharmacology and Legal Status of Kratom. The Journal of the American Osteopathic Association. 2016 Dec; 116(12):802-809. doi: 10.7556/jaoa.2016.156. [PMID: 27893147]
  • O Hayden Griffin, Jace A Daniels, Elizabeth A Gardner. Do You Get What You Paid For? An Examination of Products Advertised as Kratom. Journal of psychoactive drugs. 2016 Nov; 48(5):330-335. doi: 10.1080/02791072.2016.1229876. [PMID: 27669103]
  • Farah W Suhaimi, Nurul H M Yusoff, Rahimah Hassan, Sharif M Mansor, Visweswaran Navaratnam, Christian P Müller, Zurina Hassan. Neurobiology of Kratom and its main alkaloid mitragynine. Brain research bulletin. 2016 09; 126(Pt 1):29-40. doi: 10.1016/j.brainresbull.2016.03.015. [PMID: 27018165]
  • Andrew C Kruegel, Madalee M Gassaway, Abhijeet Kapoor, András Váradi, Susruta Majumdar, Marta Filizola, Jonathan A Javitch, Dalibor Sames. Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators. Journal of the American Chemical Society. 2016 06; 138(21):6754-64. doi: 10.1021/jacs.6b00360. [PMID: 27192616]
  • Jessica M Carpenter, Catherine A Criddle, Helaina K Craig, Zulfiqar Ali, Zhihao Zhang, Ikhlas A Khan, Kenneth J Sufka. Comparative effects of Mitragyna speciosa extract, mitragynine, and opioid agonists on thermal nociception in rats. Fitoterapia. 2016 Mar; 109(?):87-90. doi: 10.1016/j.fitote.2015.12.001. [PMID: 26688378]
  • Nurul H M Yusoff, Farah W Suhaimi, Raja K Vadivelu, Zurina Hassan, Anne Rümler, Andrea Rotter, Davide Amato, Hans C Dringenberg, Sharif M Mansor, Visweswaran Navaratnam, Christian P Müller. Abuse potential and adverse cognitive effects of mitragynine (kratom). Addiction biology. 2016 Jan; 21(1):98-110. doi: 10.1111/adb.12185. [PMID: 25262913]
  • N R Neng, S M Ahmad, H Gaspar, J M F Nogueira. Determination of mitragynine in urine matrices by bar adsorptive microextraction and HPLC analysis. Talanta. 2015 Nov; 144(?):105-9. doi: 10.1016/j.talanta.2015.05.038. [PMID: 26452798]
  • Jamie P Smith, Oliver B Sutcliffe, Craig E Banks. An overview of recent developments in the analytical detection of new psychoactive substances (NPSs). The Analyst. 2015 Aug; 140(15):4932-48. doi: 10.1039/c5an00797f. [PMID: 26031385]
  • Norsyifa Harun, Zurina Hassan, Visweswaran Navaratnam, Sharif M Mansor, Mohammed Shoaib. Discriminative stimulus properties of mitragynine (kratom) in rats. Psychopharmacology. 2015 Jul; 232(13):2227-38. doi: 10.1007/s00213-015-3866-5. [PMID: 25616583]
  • Darshan Singh, Christian P Müller, Balasingam K Vicknasingam, Sharif M Mansor. Social Functioning of Kratom (Mitragyna speciosa) Users in Malaysia. Journal of psychoactive drugs. 2015 Apr; 47(2):125-31. doi: 10.1080/02791072.2015.1012610. [PMID: 25950592]
  • Surash Ramanathan, Suhanya Parthasarathy, Vikneswaran Murugaiyah, Enrico Magosso, Soo Choon Tan, Sharif Mahsufi Mansor. Understanding the physicochemical properties of mitragynine, a principal alkaloid of Mitragyna speciosa, for preclinical evaluation. Molecules (Basel, Switzerland). 2015 Mar; 20(3):4915-27. doi: 10.3390/molecules20034915. [PMID: 25793541]
  • Iain M McIntyre, Amber Trochta, Susan Stolberg, Steven C Campman. Mitragynine 'Kratom' related fatality: a case report with postmortem concentrations. Journal of analytical toxicology. 2015 Mar; 39(2):152-5. doi: 10.1093/jat/bku137. [PMID: 25516573]
  • Markus R Meyer, Aline Schütz, Hans H Maurer. Contribution of human esterases to the metabolism of selected drugs of abuse. Toxicology letters. 2015 Jan; 232(1):159-66. doi: 10.1016/j.toxlet.2014.10.026. [PMID: 25445008]
  • Satariya Trakulsrichai, Korbtham Sathirakul, Saranya Auparakkitanon, Jatupon Krongvorakul, Jetjamnong Sueajai, Nantida Noumjad, Chonlaphat Sukasem, Winai Wananukul. Pharmacokinetics of mitragynine in man. Drug design, development and therapy. 2015; 9(?):2421-9. doi: 10.2147/dddt.s79658. [PMID: 25995615]