Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

7-Hydroxymitragynine

From Wikipedia, the free encyclopedia
Atypical Opioid analgesic compound

Pharmaceutical compound
7-Hydroxymitragynine
Clinical data
Other names7-OH; 7α-Hydroxy-7H-mitragynine;[1]9-Methoxycorynantheidine hydroxyindolenine[1]
Dependence
liability
High
Addiction
liability
High[2]
Routes of
administration
Oral
Drug classOpioid
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolitesMitragynine pseudoindoxyl
Identifiers
  • Methyl (2E)-2-[(2S,3S,7aS,12bS)-3-ethyl-7a-hydroxy-8-methoxy-1,2,3,4,6,7,7a,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H30N2O5
Molar mass414.502 g·mol−1
3D model (JSmol)
  • CC[C@@H]1CN2CC[C@@]3(O)C(=Nc4cccc(OC)c34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

  • CC[C@@H]1CN2CC[C@@]3(O)C(=NC4=CC=CC(OC)=C34)[C@@H]2C[C@@H]1\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-MIT, often simply referred to as7-OH) is aterpenoidindolealkaloid present in the plantMitragyna speciosa (the leaves of which are commonly known askratom).[3] It was first described in 1994.[4] In humans, it is produced as an active metabolite ofmitragynine via hepatic oxidation.[5] 7-OH exhibits greater binding affinity toμ-opioid receptors (MOR) than mitragynine.[citation needed]

Pharmacology

[edit]

7-OH-MIT, like mitragynine, appears to be a mixed opioid receptoragonist/antagonist, with recent research indicating that it acts as apartial agonist atμ-opioid receptors and as a competitive antagonist atδ- andκ-opioid receptors.[6][7] Both 7-OH-MIT and mitragynine do not appear to activate theβ-arrestin pathway, distinguishing it from traditionalopiate andopioid chemicals.[6]A study has found the binding affinity of 7-OH-MIT to beμ-opioid receptor (MOR) 37 (± 4) nM andδ-opioid receptor (DOR) 91 (± 8) nM andκ-opioid receptor (KOR) 132 (± 7) nM.[8]Another study found the binding affinity of 7-OH-MIT to be MOR 16 (± 1) nM and DOR 137 (± 21) nM and KOR 133 (± 37) nM.[9]Another study found the binding affinity of 7-OH-MIT to be MOR 13.5 nM, DOR 155 nM, and KOR 123 nM.[9] Cross-tolerance to morphine was evident in mice rendered tolerant to 7-hydroxymitragynine and vice versa.Naloxone-induced withdrawal signs were elicited equally in mice chronically treated with 7-hydroxymitragynine ormorphine.[10]

Synthesis

[edit]

In natural kratom leaves, 7-hydroxymitragynine is only present in small amounts, comprising less than 2% of overall alkaloid content.[11] Therefore, extracting 7-OH-MIT in high concentrations directly from natural kratom leaves is not practical. Instead, 7-hydroxymitragynine can be producedsemisynthetically via the oxidation of mitragynine.[5]

Society and culture

[edit]

7-OH has been rising in popularity as arecreational drug, particularly in theUnited States. Its ability to bind to opioid receptors can cause addictive effects. In an electrical stimulation test using guinea-pig ileum, 7-OH performed 13 times greater pain relief than that of morphine.[12] The drug's novelty has meant that it has increasingly been sold unregulated over the counter in gas stations and smoke shops, often in highly concentrated "candy-like" or pill form alongsidekratom powder and other supplements with little to no information provided to consumers about its effects.[11]

According to the United States Poison Control Center, the number of cases relating to kratom-based products such as 7-OH have increased from under 200 in 2014 to 1600 in 2024, with approximately 40% of 7-OH reports coming from individuals who were abusing the drug.[13]

Legal status

[edit]

United States

[edit]

In July 2025, theFood and Drug Administration (FDA) formally recommended that theDrug Enforcement Administration (DEA) classify 7-hydroxymitragynine as acontrolled substance.[14] This action is not directed towardMitragyna speciosa itself, which will remain unaffected by regulation of 7-OH.[15] Despite claims by marketers for products that contain 7-OH that they can be used to treatanxiety and pain, the drug is not approved by the FDA for any medical use or as a food supplement.[16]

On August 13, 2025, Florida attorney generalJames Uthmeier announced an emergency rule placing 7-hydroxymitragynine into schedule I status under Florida state law, effectively outlawing the substance and removing it from all headshops and similar stores from the state.[17][18][19]

Research

[edit]

Studies on 7-hydroxymitragynine's safety have been unable to identify anLD50 orally with no deaths occurring.[20] 7-hydroxymitragynine has been described as a "prototypical" compound to develop a new generation of opioids with an improved safety profile.[21]

See also

[edit]

References

[edit]
  1. ^abChemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)
  2. ^Reissig CJ, Chiapperino D, Seitz A, Lee R, Radin R, McAninch J.7-Hydroxymitragynine (7-OH): An Assessment of the Scientific Data and Toxicological Concerns Around an Emerging Opioid Threat (Report).
  3. ^Matsumoto K, Horie S, Ishikawa H, Takayama H, Aimi N, Ponglux D, et al. (March 2004). "Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active atypical 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.
  4. ^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.Bibcode:1994PlMed..60..580P.doi:10.1055/s-2006-959578.PMID 17236085.S2CID 260252538.
  5. ^abKarunakaran T, Marimuthu Y, Rusmadi NN, Firouz NS, Jenis J, Kumar US, et al. (2024-10-10). "Chemistry and toxicity of 7-hydroxymitragynine (7-OHMG): an updated review on the oxidized derivative of mitragynine".Phytochemistry Reviews.24 (5):4051–4064.Bibcode:2025PChRv..24.4051G.doi:10.1007/s11101-024-10029-x.ISSN 1572-980X.
  6. ^abEastlack 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.
  7. ^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.
  8. ^Váradi A, Marrone GF, Palmer TC, Narayan A, Szabó MR, Le Rouzic V, et al. (2016)."Mitragynine/Corynantheidine Pseudoindoxyls as Opioid Analgesics with Mu Agonism and Delta Antagonism, Which do Not Recruit β-Arrestin-2".Journal of Medicinal Chemistry.59 (18):8381–8397.doi:10.1021/acs.jmedchem.6b00748.PMC 5344672.PMID 27556704.
  9. ^abTakayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, et al. (2002)."Studies on the Synthesis and Opioid Agonistic Activities of Mitragynine-Related Indole Alkaloids: Discovery of Opioid Agonists Structurally Different from Other Opioid Ligands".Journal of Medicinal Chemistry.45 (9):1949–1956.doi:10.1021/jm010576e.PMID 11960505.
  10. ^Matsumoto K, Horie S, Takayama H, Ishikawa H, Aimi N, Ponglux D, et al. (2005). "Antinociception, tolerance and withdrawal symptoms induced by 7-hydroxymitragynine, an alkaloid from the Thai medicinal herb Mitragyna speciosa".Life Sciences.78 (1):2–7.doi:10.1016/j.lfs.2004.10.086.PMID 16169018.
  11. ^abReissig CJ, Chiapperino D, Seitz A, Lee R, Radin R, McAninch J (2025)."7-Hydroxymitragynine (7-OH): An Assessment of the Scientific Data and Toxicological Concerns Around an Emerging Opioid Threat".Food and Drug Administration: 4.7-OH is a naturally occurring substance in the kratom plant (Mitragyna speciosa), but only a minor constituent that comprises less than 2% of the total alkaloid content in natural kratom leaves.
  12. ^Reissig CJ, Chiapperino D, Seitz A, Lee R, Radin R, McAninch J.7-Hydroxymitragynine (7-OH): An Assessment of the Scientific Data and Toxicological Concerns Around an Emerging Opioid Threat (Report). U.S. Drug and Food Administration (FDA) Center for Drug Evaluation and Research (CDER). p. 14.7-OH displayed approximately 13-fold greater potency than morphine
  13. ^Office of the Commissioner (2025-07-30)."Hiding in Plain Sight: 7-OH Products".FDA. Retrieved2025-08-05.
  14. ^"US health officials crack down on kratom-related products after complaints from supplement industry".WHEC. Associated Press. 2025-07-29. Retrieved2025-07-29.
  15. ^U.S. Food and Drug Administration (July 29, 2025)."FDA Takes Steps to Restrict 7-OH Opioid Products Threatening American Consumers".FDA. RetrievedAugust 18, 2025.
  16. ^"Products Containing 7-OH Can Cause Serious Harm".Drugs.com. Retrieved2025-08-05.
  17. ^"Attorney General James Uthmeier Files Emergency Rule; Immediately Removing Dangerous 7-OH from Store Shelves | My Florida Legal".
  18. ^"Florida AG announces ban on "7-OH" products". 13 August 2025.
  19. ^<https://www.fox13news.com/news/florida-ag-uthmeier-taking-emergency-action-against-new-synthetic-drug-7-oh
  20. ^Smith LC, Lin L, Hwang CS, Zhou B, Kubitz DM, Wang H, et al. (2019)."Lateral Flow Assessment and Unanticipated Toxicity of Kratom".Chemical Research in Toxicology.32 (1):113–121.doi:10.1021/acs.chemrestox.8b00218.PMC 6662923.PMID 30380840.
  21. ^Matsumoto K, Narita M, Muramatsu N, Nakayama T, Misawa K, Kitajima M, et al. (2014)."Orally active opioid μ/δ dual agonist MGM-16, a derivative of the indole alkaloid mitragynine, exhibits potent antiallodynic effect on neuropathic pain in mice".The Journal of Pharmacology and Experimental Therapeutics.348 (3):383–392.doi:10.1124/jpet.113.208108.PMC 6067406.PMID 24345467.


μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
Retrieved from "https://en.wikipedia.org/w/index.php?title=7-Hydroxymitragynine&oldid=1323622836"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp