Mitragynine

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Mitragynine
Mitragynine2DACS.svg
Mitragynine2cropped.png
Names
IUPAC name
(E)-2-[(2S,3S)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b- octahydroindolo[3,2-h]quinolizin-2-yl]-3- methoxyprop-2-enoic acid methyl ester
Identifiers
6202-22-8 N
ChEMBL ChEMBL299031 YesY
ChemSpider 2298865 YesY
Jmol 3D model Interactive image
PubChem 3034396
  • 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 YesY
    Key: LELBFTMXCIIKKX-QVRQZEMUSA-N YesY
  • 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
    Key: LELBFTMXCIIKKX-QVRQZEMUBK
  • O=C(/C([C@H]1C[C@H]2C3=C(CCN2C[C@H]1CC)C4=C(OC)C=CC=C4N3[H])=C/OC)OC
Properties
C23H30N2O4
Molar mass 398.495
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Mitragynine, an indole alkaloid, is the most abundant active alkaloid in the plant Mitragyna speciosa, commonly known as Kratom[1] and "Biak-Biak".[2]

Subjective perceptions

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.[3][4][5][6] 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).[7]

Pharmacology

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.[8][9] 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. The extent to which this minor but more potent mu agonist constituent of the plant contributes to the subjective effects of Kratom consumption is still unclear.[10][11]

Pharmacokinetics

Mitragynine has been studied in chronic users. It undergoes extensive hepatic metabolism with linear kinetics and long half life.[12] A large volume of distribution with two compartments is seen.

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.[13]

Structure

It is structurally related to both the yohimbe alkaloids and, more distantly, voacangine. Chemically, mitragynine is 9-methoxy-corynantheidine.

Dose

Dry kratom leaf contains roughly 1-6% mitragynine.[14] A typical dose ranges from 15 mg to 65 mg[citation needed]. A notable distinction between mitragynine and traditional opioids is that mitragynine does not cause hypoventilation (respiratory depression) and therefore does not carry the primary safety risk associated with traditional opioids, most likely due to its agonism of the δ-opioid receptor.[citation needed]

Synthesis

The first total synthesis of mitragynine was reported by Takayama et al. in 1995.[15]

Chemical properties

Physically the freebase is a white, amorphous powder. It is soluble in alcohol, chloroform and acetic acid.

See also

References

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External links

Further reading

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