7-Hydroxymitragynine
Opioid analgesic compound From Wikipedia, the free encyclopedia
Opioid analgesic compound From Wikipedia, the free encyclopedia
7-Hydroxymitragynine (7-OH) is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as kratom.[2] It was first described in 1994[3] and is a natural product derived from mitragynine present in the kratom leaf. 7-OH binds to opioid receptors like mitragynine, but research suggests that 7-OH binds with greater efficacy.[4]
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Other names | 7α-Hydroxy-7H-mitragynine;[1] 9-Methoxycorynantheidine hydroxyindolenine[1] |
Routes of administration | By mouth |
Drug class | Opioid |
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Metabolites | Mitragynine pseudoindoxyl |
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Formula | C23H30N2O5 |
Molar mass | 414.502 g·mol−1 |
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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] 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]
7-Hydroxymitragynine can convert into mitragynine up to 45% in human liver microsomes over a two-hour incubation and was degraded up to 27% in simulated gastric fluid and degraded up to 6% in simulated intestinal fluid.[7] 7-Hydroxymitragynine can metabolize to mitragynine pseudoindoxyl in the blood but not in the liver.[8][9] Interestingly, this even more potent opioid was revealed to exist in a mixture of stereoisomers in biological systems.[9]
Compound | Affinities (Ki ) | Ratio | Ref | ||
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MOR | DOR | KOR | 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] |
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