7-Hydroxymitragynine

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7-Hydroxymitragynine
Stereo, Kekulé, skeletal formula of 7-hydroxymitragynine with an explicit hydrogen added
7-Hydroxymitragynine is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as Kratom.
Names
Systematic IUPAC name
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
Other names
7α-Hydroxy-7H-mitragynine;[1] 9-Methoxycorynantheidine hydroxyindolenine[1]
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • 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
  • 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
Properties
C23H30N2O5
Molar mass 414.502 g·mol−1
log P 1.266
Acidity (pKa) 12.203
Basicity (pKb) 1.794
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

7-Hydroxymitragynine (7-OH) is a

opioid receptors like mitragynine, but research suggests that 7-OH binds with greater potency.[5]

7-Acetoxymitragynine

Dependence and withdrawal

Main article: Mitragynine § Dependence and withdrawal

Pharmacology

7-Hydroxymitragynine, like mitragynine, appears to be a mixed opioid receptor

β-arrestin pathway like traditional opioids, meaning symptoms such as respiratory depression, constipation and sedation are much less pronounced.[6]

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.[6]

Metabolism

After a kratom study, it was revealed that 7-OH converts into mitragynine pseudoindoxyl.[8][9] Interestingly, this even more potent opioid was revealed to exist in a mixture of stereoisomers in biological systems.[9]

Mitragynine Pseudoindoxyl
Mitragyna speciosa alkaloids at opioid receptors
Compound
Ki
Tooltip Inhibitor constant)		 Ratio Ref
MOR
Tooltip μ-Opioid receptor
DOR
Tooltip δ-Opioid receptor
KOR
Tooltip κ-Opioid receptor		 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]

See also

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. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. PMID 14969718
    .
  4. S2CID 260252538
    .
  5. S2CID 24009429
    .
  6. ^
    PMID 31994019
    .
  7. ^
    PMID 28072812
    .
  8. PMID 27556704
    .
  9. ^
    PMID 33344889
    .
  10. ^
    PMID 11960505
    .

Further reading
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