Mitragynine
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IUPAC name
Methyl (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),11(16),12,14-tetraen-4-yl]-3-methoxyprop-2-enoate
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| Identifiers | |
4098-40-2 
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| 3D model (Jmol) | Interactive image |
| ChEMBL |
ChEMBL299031 
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| ChemSpider |
2298865
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| KEGG |
C09226
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| PubChem | 3034396 |
| UNII |
EP479K822J
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| Properties | |
| C23H30N2O4 | |
| Molar mass | 398.4953 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is ?) |
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| Infobox references | |
Mitragynine is an indole-based opioid and the most abundant active alkaloid in the plant Mitragyna speciosa, commonly known as kratom and biak-biak. Dry kratom leaf contains roughly 1.2–2.1% mitragynine.
In spite of the fact that mitragynine has sometimes been touted and used as a “legal opioid,” few scientific studies have addressed the psychoactive properties of mitragynine. Most of the available information is based on anecdotal reports and patient experiences. The general subjective effects of mitragynine have been summarized in various reviews and include improved mood and analgesia, with some subjects experiencing relaxation and others stimulation (paradoxical effects).
Mitragynine itself acts primarily via μ-opioid receptors, though its oxidation product mitragynine pseudoindoxyl, acts as an even more potent and selective μ-opioid agonist but with less affinity for δ or κ receptors. Another alkaloid with a major contribution to the μ-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 μ-opioid partial agonist. The extent to which this minor but more potent partial mu agonist constituent of the plant contributes to the subjective effects of Kratom consumption is still unclear.
Mitragynine has been studied in chronic users. It undergoes extensive hepatic metabolism with linear kinetics and long half life.
Blood mitragynine concentrations are expected to be in a range of 10–50 μg/L in persons using the drug recreationally. Detection in body fluids is typically by liquid chromatography-mass spectrometry.
It is structurally related to both the yohimbe alkaloids and, more distantly, voacangine. Chemically, mitragynine is 9-methoxy-corynantheidine.
The first total synthesis of mitragynine was reported by Takayama et al. in 1995.
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