7-Hydroxymitragynine

In this article we are going to explore 7-Hydroxymitragynine, a topic that has captured the attention of many over the years. From its origins to its impact on modern society, 7-Hydroxymitragynine has been the subject of debate and discussion. As we delve deeper into this topic, we will discover its implications in different areas, as well as the advances and challenges that surround it. Using a critical and analytical approach, we will examine the importance of 7-Hydroxymitragynine in today's world and how it has shaped our perception and understanding of it. Through this article, we hope to offer a deeper and more complete vision of 7-Hydroxymitragynine, inviting our readers to reflect on its relevance and meaning today.

7-Hydroxymitragynine
Clinical data
Other names7α-Hydroxy-7H-mitragynine;[1] 9-Methoxycorynantheidine hydroxyindolenine[1]
Routes of
administration		By mouth
Drug classOpioid
ATC code
  • None
Legal status
Legal status
  • BR: Class F1 (Prohibited narcotics)
  • US: Unscheduled
Pharmacokinetic data
MetabolitesMitragynine pseudoindoxyl
Identifiers
  • Methyl (2E)-2-quinolizin-2-yl]-3-methoxyprop-2-enoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30N2O5
Molar mass414.502 g·mol−1
3D model (JSmol)
  • CC1CN2CC3(O)C(=Nc4cccc(OC)c34)2C1\C(=C/OC)C(=O)OC

  • CC1CN2CC3(O)C(=NC4=CC=CC(OC)=C34)2C1\C(=C/OC)C(=O)OC
  • InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15+,18+,23+/m1/s1 checkY
  • Key:RYENLSMHLCNXJT-CYXFISRXSA-N checkY

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, commonly known as kratom. 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]

Recent developments in the market have introduced semi-synthetic 7-OH products, which differ from traditional kratom preparations in both concentration and route of administration. These novel products often contain up to 98% 7-OH and are marketed in formulations such as sublingual tablets and nasal sprays. Some of these formulations bypass first-pass metabolism, significantly increasing bioavailability and potentially amplifying their opioid-like effects.[6]

Pharmacology

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.[7][8] 7-OH does not appear to activate the β-arrestin pathway, distinguising it from traditional opiate & opioid chemicals.[7] It shares this trait with mitragynine.

References

  1. ^ a b Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.