Mitragynine
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| Mitragynine | |
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| IUPAC name | Mitragynine |
| Identifiers | |
| CAS number | [4098-40-2] |
| Properties | |
| Molecular formula | C23H30N2O4 |
| Molar mass | 398.2206 g/mol |
| Melting point |
39 - 41 °C |
| Boiling point |
110 - 115.6 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Mitragynine, an indole alkaloid, is the most abundant active alkaloid in the plant Mitragyna speciosa, commonly known as Kratom. In small doses its activity is reported to be stimulant like, while in higher doses more opiate like. These effects agree with the profile of mitragynine's actions developed by study of its action on the brain. It has been shown to be adrenergic (like some related alkaloids from yohimbe) at lower doses while at higher doses mitragynine acts on the mu and delta opiate receptors. The mu opiate receptors are responsible for the enjoyable effects of the opiates, analgesia, and physical dependence. Its potential for treating drug addiction, perhaps in combination with ibogaine, is being investigated. It is orally active.
Mitragynine was isolated in 1907 by D. Hooper, a process repeated in 1921 by E. Field who gave the alkaloid its name. Its structure was first fully determined in 1964 by D. Zacharias, R. Rosenstein and E. Jeffrey.
It is structurally related to both the yohimbe alkaloids and, more distantly, voacangine. It is even more distantly related to other tryptamine-based psychedelic drugs such as psilocybin or LSD. Chemically, mitragynine is 9-methoxy-corynantheidine.
Mitragynine itself acts primarily via μ-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 δ-opioid agonist with little affinity for μ or κ receptors.[1] 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 agonist.[2]
[edit] Chemical traits
Physically the freebase is a white, amorphous powder. It is soluble in alcohol, chloroform and acetic acid.
[edit] References
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The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking. |
- ^ Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, Koyama F, Matsumoto K, Moriyama T, Yamamoto LT, Watanabe K, Murayama T, Horie S. 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. 2002; 45: 1949-1956.
- ^ Takayama H. Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa. Chem. Pharm. Bull. 2004; 52(8):916—928.
- Takayama H.; Maeda M.; Ohbayashi S.; Kitajima M.; Sakai S.-i.; Aimi N. (1995). "The First Total Synthesis of (-)-Mitragynine, An Analgesic Indole Alkaloid in Mitragyna speciosa". Tetrahedron Letters 36 (51): 9337–9340. doi:.
[edit] See also
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