7-Hydroxymitragynine
7-Hydroxymitragynine (7-OH) is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as kratom.
It was first described in 1994 and is a natural product derived from the mitragynine present in the kratom leaf. 7-OH binds to opioid receptors like mitragynine, but research suggests that 7-OH binds with greater potency.
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| Systematic IUPAC name Methyl (2E)-2-[(2S,3S,7aS,12bS)-3-ethyl-7a-hydroxy-8-methoxy-1,2,3,4,6,7,7a,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate | |
| Other names 7α-Hydroxy-7H-mitragynine; 9-Methoxycorynantheidine hydroxyindolenine | |
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| Properties | |
| C23H30N2O5 | |
| Molar mass | 414.502 g·mol−1 |
| log P | 1.266 |
| Acidity (pKa) | 12.203 |
| Basicity (pKb) | 1.794 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Dependence and withdrawal
Pharmacology
7-Hydroxymitragynine, like mitragynine, appears to be a mixed opioid receptor agonist/antagonist, acting as a partial agonist at μ-opioid receptors and as a competitive antagonist at δ- and κ-opioid receptors. It also acts on alpha 2 adrenergic and 5-HT2A receptors. Evidence suggests that 7-OH is more potent than both mitragynine and morphine. 7-OH does not activate the β-arrestin pathway like traditional opioids, meaning symptoms such as respiratory depression, constipation and sedation are much less pronounced.
7-OH is generated from mitragynine in vivo by hepatic metabolism and may account for a significant portion of the effects traditionally associated with mitragynine. Although 7-OH occurs naturally in kratom leaves, it does so in such low amounts that any ingested 7-OH is inconsequential compared to the 7-OH generated in the body.
Metabolism
After a kratom study, it was revealed that 7-OH converts into mitragynine pseudoindoxyl. Interestingly, this even more potent opioid was revealed to exist in a mixture of stereoisomers in biological systems.
| Compound | Affinities (Ki) | Ratio | Ref | ||
|---|---|---|---|---|---|
| MOR | DOR | KOR | MOR:DOR:KOR | ||
| 7-Hydroxymitragynine | 13.5 | 155 | 123 | 1:11:9 | |
| Mitragynine | 7.24 | 60.3 | 1,100 | 1:8:152 | |
| Mitragynine pseudoindoxyl | 0.087 | 3.02 | 79.4 | 1:35:913 | |
See also
- Ajmalicine
- Mitragynine
- Mitragynine pseudoindoxyl
- Mitraphylline
- β-Prodine - molecule overlaying 7-hydroxymitragynine's opioid QSAR (Quantitative structure-activity relationship)
References
Further reading
- Takayama H (August 2004). "Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa". Chemical & Pharmaceutical Bulletin. 52 (8): 916–928. doi:10.1248/cpb.52.916. PMID 15304982.
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