7-Hydroxymitragynine is a
terpenoid
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...
indole
Indole is an aromatic heterocyclic organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c ...
alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
from the plant ''
Mitragyna speciosa
''Mitragyna speciosa'' (commonly known as kratom, an herbal leaf from a tree of the Rubiaceae family, ) is a tropical evergreen tree in the coffee family native to Southeast Asia. It is indigenous to Thailand, Indonesia, Malaysia, Myanmar, and ...
'', commonly known as Kratom.
It is often referred to as ‘7-OH’. It was first described in 1994 and is a natural product derived from the
mitragynine present in the
Kratom leaf. It is considered an oxidized derivative and active metabolite of mitragynine. 7-OH binds to
opioid receptors like mitragynine, but research suggests that 7-OH binds with greater potency and contributes heavily to the analgesic activity of mitragynine as a metabolite.
Metabolism
After a kratom study, it was revealed that 7-OH converts into
Mitragynine pseudoindoxyl.
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 the
δ- and
κ-opioid receptors.
Evidence suggests that 7-OH is more potent than both mitragynine and
morphine
Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. T ...
. 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.
See also
*
Ajmalicine
Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under numerous brand names including Card-Lamuran, Circolene, Cristanyl, Duxil, Duxor, Hydroxysarp ...
*
Mitragynine
*
Mitragynine pseudoindoxyl
*
Mitraphylline
*
β-Prodine - molecule overlaying 7-hydroxymitragynine's opioid QSAR (Quantitative structure-activity relationship)
References
Further reading
*
{{DEFAULTSORT:Hydroxymitragynine, 7-
Tryptamine alkaloids
Opioids
Biased ligands
Indoloquinolizines
Mu-opioid receptor agonists
Tertiary alcohols
Ethers
Conjugated dienes