Английская Википедия:7-Hydroxymitragynine
Шаблон:Short description Шаблон:Chembox 7-Hydroxymitragynine (7-OH) is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as kratom.[1] It was first described in 1994[2] 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[3] and contributes heavily to the analgesic activity of mitragynine as a metabolite.[4]
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.[5][6] It also acts on alpha 2 adrenergic and 5-HT2A receptors.[6] 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.[5]
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.[5]
Metabolism
After a kratom study, it was revealed that 7-OH converts into mitragynine pseudoindoxyl.[7][8] Interestingly, this even more potent opioid was revealed to exist in a mixture of stereoisomers in biological systems.[9]
| Compound | Affinities (Шаблон:Abbrlink) | Ratio | Ref | ||
|---|---|---|---|---|---|
| Шаблон:Abbrlink | Шаблон:Abbrlink | Шаблон:Abbrlink | MOR:DOR:KOR | ||
| 7-Hydroxymitragynine | 13.5 | 155 | 123 | 1:11:9 | [10] |
| Mitragynine | 7.24 | 60.3 | 1,100 | 1:8:152 | [10] |
| Mitragynine pseudoindoxyl | 0.087 | 3.02 | 79.4 | 1:35:913 | [10] |
See also
- Ajmalicine
- Mitragynine
- Mitragynine pseudoindoxyl
- Mitraphylline
- β-Prodine - molecule overlaying 7-hydroxymitragynine's opioid QSAR (Quantitative structure-activity relationship)
References
Further reading
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