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| {{chembox | |||
| | ImageFile = Mitragynine.png | |||
| | ImageSize = | |||
| | IUPACName = (E)-2-quinolizin-2-yl]-3- methoxyprop-2-enoic acid methyl ester | |||
| | OtherNames = | |||
| | Section1 = {{Chembox Identifiers | |||
| | ChemSpiderID = 2298865 | |||
| | InChI = 1/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 | |||
| | InChIKey = LELBFTMXCIIKKX-QVRQZEMUBK | |||
| | StdInChI = 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 | |||
| | StdInChIKey = LELBFTMXCIIKKX-QVRQZEMUSA-N | |||
| | CASNo=6202-22-8 | |||
| | PubChem = 3034396 | |||
| | SMILES = O=C(OC)\C(=C\OC)4C3c2nc1cccc(OC)c1c2CCN3C4CC | |||
| }} | |||
| | Section2 = {{Chembox Properties | |||
| | Formula=C<sub>23</sub>H<sub>30</sub>N<sub>2</sub>O<sub>4</sub> | |||
| | MolarMass=398.4953 | |||
| | Appearance= | |||
| | Density= | |||
| | MeltingPt= | |||
| | BoilingPt= | |||
| | Solubility= | |||
| }} | |||
| | Section3 = {{Chembox Hazards | |||
| | MainHazards= | |||
| | FlashPt= | |||
| | Autoignition= | |||
| }} | |||
| }} | |||
| '''Mitragynine''', an indole alkaloid, is the most abundant active ] in the plant '']'', commonly known as ].<ref name="pmid3419199">{{cite journal | author = Jansen KL, Prast CJ | title = Ethnopharmacology of kratom and the Mitragyna alkaloids | journal = J Ethnopharmacol | volume = 23 | issue = 1 | pages = 115–9 | year = 1988 | pmid = 3419199 | doi = 10.1016/0378-8741(88)90121-3| url = }}</ref> | |||
| ==Pharmacology== | |||
| 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 ]) 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 ], is being investigated{{Who|date=August 2010}}. It is orally active. | |||
| Mitragynine itself acts primarily via μ-opioid receptors, although its oxidation product ], which is likely to be a major component of kratom that has been aged or stored for extended periods, acts as a fairly selective ] ] with little affinity for μ or κ receptors.<ref name="pmid11960505">{{cite journal | author = 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 | title = Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands | journal = J. Med. Chem. | volume = 45 | issue = 9 | pages = 1949–56 | year = 2002 | month = April | pmid = 11960505 | doi = 10.1021/jm010576e | url = }}</ref> Another alkaloid with a major contribution to the μ-opioid activity of the kratom plant is the related compound ], which while present in the plant in much smaller quantities than mitragynine, is a much more potent μ-opioid agonist.<ref name="pmid15304982">{{cite journal | author = Takayama H | title = Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa | journal = Chem. Pharm. Bull. | volume = 52 | issue = 8 | pages = 916–28 | year = 2004 | month = August | pmid = 15304982 | doi = 10.1248/cpb.52.916| url = http://joi.jlc.jst.go.jp/JST.JSTAGE/cpb/52.916?from=PubMed| format = {{Dead link|date=June 2008}} – <sup></sup> }}</ref> | |||
| ==Discovery== | |||
| 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. | |||
| ==Structure== | |||
| It is structurally related to both the ] ]s and, more distantly, ]. Chemically, mitragynine is 9-methoxy-corynantheidine. | |||
| ==Dose== | |||
| Dry kratom leaf contains roughly 0.25% mitragynine. A typical dose ranges from 15 mg to 65 mg. | |||
| ==Synthesis== | |||
| The first ] of mitragynine was reported by Takayama et al. in 1995.<ref name="Takayama_1995">{{cite journal | author = Takayama H.; Maeda M.; Ohbayashi S.; Kitajima M.; Sakai S.-i.; Aimi N. | title = The First Total Synthesis of (-)-Mitragynine, An Analgesic Indole Alkaloid in Mitragyna speciosa | journal = Tetrahedron Letters | volume = 36 | issue = 51 | year = 1995 | pages = 9337–9340 | doi = 10.1016/0040-4039(95)02022-H }}</ref> | |||
| ==Chemical properties== | |||
| Physically the ] is a white, amorphous powder. It is soluble in alcohol, chloroform and acetic acid. | |||
| ==References== | |||
| {{Reflist|2}} | |||
| ==See also== | |||
| *] | |||
| *] | |||
| *] | |||
| *] | |||
| {{Opioids}} | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||