Mitragynine is an indole-based opioid-receptor agonist 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.
Video Mitragynine
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. 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).
Maps Mitragynine
Pharmacology
Mitragynine itself acts primarily via ?-opioid receptors, though its oxidation product mitragynine pseudoindoxyl, acts as a selective ?-opioid agonist but with less affinity for ? or ? 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 partial agonist.
Derivatives
Research on mitragynine structure-activity relationships lead to discovery of new potent opioid agonists, notably some C10-halogen and 2,3-ethylene glycol bridged derivatives of 7-hydroxymitragynine. The most potent one is the 10-fluoro ethylene glycol adduct of 7-hydroxymitragynine with a potency 4-fold higher than 7-hydroxymitragynine. Other modification lead to 2,3-dihydro derivatives such as MGM-15, prepared by reduction of 7-hydroxymitragynine with sodium borohydride. The antinociceptive effect of MGM-15 is approximately 15 and 50 times more potent than that of morphine after subcutaneous and oral administration.
Pharmacokinetics
Mitragynine has been studied in chronic users. It undergoes extensive hepatic metabolism with linear kinetics and long half life.
Detection in body fluids
Blood mitragynine concentrations are expected to be in a range of 10-50 ?g/L in persons using the drug recreationally. Detection in body fluids is typically by liquid chromatography-mass spectrometry.
Structure
It is structurally related to yohimbine but shows a totally different pharmacology.
Synthesis
The first total synthesis of mitragynine was reported by Takayama et al. in 1995.
See also
- 7-Hydroxymitragynine
- Mitragynine pseudoindoxyl
- Mitraphylline
- Yohimbine
References
External links
- The Malaysian Journal of Analytical Sciences, Vol 15 No 1: A simple and cost effective isolation and purification protocol of mitragynine from Mitragyna speciosa korth (ketum) leaves.
Further reading
- Mitragynine on ToxNet CASRN: 4098-40-2
Source of article : Wikipedia
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