7-Hydroxymitragynine
 | |
 | |
| Clinical data | |
|---|---|
| Other names | 7α-Hydroxy-7H-mitragynine;[1] 9-Methoxycorynantheidine hydroxyindolenine[1] |
| Routes of administration | By mouth; inhalation |
| Drug class | Opioid |
| ATC code |
|
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Metabolites | Mitragynine pseudoindoxyl |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C23H30N2O5 |
| Molar mass | 414.502 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
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 human metabolite metabolized from mitragynine present in the Mitragyna speciosa. 7-OH binds to opioid receptors like mitragynine, but research suggests that 7-OH binds with greater efficacy.[4]
7-Hydroxymitragynine (7-OH), a metabolite of the psychoactive botanical kratom, exhibits significantly higher binding affinity to mu-opioid receptors (MOR) than morphine, with estimates ranging from 14 to 22 times greater potency. Although kratom's primary alkaloid, mitragynine, is associated with lower abuse potential and moderate safety, 7-OH demonstrates opioid-like effects and can substitute for morphine in a dose-dependent manner, raising concerns about its potential for physical dependence and addiction.[5]
Pharmacology
[edit]7-Hydroxymitragynine, like mitragynine, appears to be a mixed opioid receptor agonist/antagonist, with recent research indicating that it acts as a partial agonist at μ-opioid receptors and as a competitive antagonist at δ- and κ-opioid receptors.[6][7] 7-OH does not appear to activate the β-arrestin pathway, distinguishing it from traditional opiate & opioid chemicals.[6] It shares this trait with mitragynine.
Synthesis
[edit]In natural kratom leaves, 7-Hydroxymitragynine is only present in extremely small amounts (around 0.01% to 0.04% of total alkaloid content). Therefore, extracting 7-OH in high concentrations directly from natural kratom leave is not feasible due to the natural yield being too low. This means that all high-concentration 7-OH products must be produced via chemical synthesis rather than simple extraction. The most common methods usually involve chemically modifying mitragynine, the most abundant alkaloid in kratom, to artificially increase 7-OH concentration via oxidation reactions. This process often involves the usage of reagents such as hydrogen peroxide, enzymes, or strong acids to convert the mitragynine into 7-OH.
References
[edit]- ^ a b Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
- ^ Matsumoto K, Horie S, Ishikawa H, Takayama H, Aimi N, Ponglux D, Watanabe K (March 2004). "Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa". Life Sciences. 74 (17): 2143–2155. doi:10.1016/j.lfs.2003.09.054. PMID 14969718.
- ^ Ponglux D, Wongseripipatana S, Takayama H, Kikuchi M, Kurihara M, Kitajima M, et al. (December 1994). "A New Indole Alkaloid, 7 alpha-Hydroxy-7H-mitragynine, from Mitragyna speciosa in Thailand". Planta Medica. 60 (6): 580–581. doi:10.1055/s-2006-959578. PMID 17236085. S2CID 260252538.
- ^ Kruegel AC, Grundmann O (May 2018). "The medicinal chemistry and neuropharmacology of kratom: A preliminary discussion of a promising medicinal plant and analysis of its potential for abuse". Neuropharmacology. 134 (Pt A): 108–120. doi:10.1016/j.neuropharm.2017.08.026. PMID 28830758. S2CID 24009429.
- ^ Smith KE, Boyer EW, Grundmann O, McCurdy CR, Sharma A (2024). "The rise of novel, semi-synthetic 7-hydroxymitragnine products". Addiction. doi:10.1111/add.16728. PMID 39627873.
- ^ a b Eastlack SC, Cornett EM, Kaye AD (June 2020). "Kratom-Pharmacology, Clinical Implications, and Outlook: A Comprehensive Review". Pain and Therapy. 9 (1): 55–69. doi:10.1007/s40122-020-00151-x. PMC 7203303. PMID 31994019.
- ^ Chang-Chien GC, Odonkor CA, Amorapanth P (2017). "Is Kratom the New 'Legal High' on the Block?: The Case of an Emerging Opioid Receptor Agonist with Substance Abuse Potential". Pain Physician. 20 (1): E195 – E198. doi:10.36076/ppj.2017.1.E195. PMID 28072812.