Structure via PubChem · Public domain (PubChem)
7-hydroxymitragynine
Sign in to save7-Hydroxymitragynine (7-OH-MIT, often simply referred to as 7-OH) is a terpenoid indole alkaloid present in the plant Mitragyna speciosa (the leaves of which are commonly known as kratom). It was first described in 1994. In humans, it is produced as an active metabolite of mitragynine via hepatic oxidation.
Key facts
- Drug.drug_name
- 7-Hydroxymitragynine
- Drug.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
- Drug.image
- 7-hydroxymitragynine2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- 7-OH-mitragynine.png
- Drug.image_class2
- bg-transparent
- Drug.legal_BR
- F1
- Drug.legal_US
- Unscheduled
- Drug.dependency_liability
- High
- Drug.addiction_liability
- High
- Drug.routes_of_administration
- Oral
- Drug.metabolites
- Mitragynine pseudoindoxyl
- Drug.CAS_number
- 174418-82-7
- Drug.ATC_prefix
- None
- Drug.PubChem
- 44301524
- Drug.ChemSpiderID
- 23152144
- Drug.UNII
- 2T3TWA75R0
- Drug.ChEMBL
- 61630
via Wikipedia infobox
Chemical data
- Formula
- C23H30N2O5
- Molecular weight
- 414.5 g/mol
- IUPAC name
- methyl (E)-2-[(2S,3S,7aS,12bS)-3-ethyl-7a-hydroxy-8-methoxy-2,3,4,6,7,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
- SMILES
- CC[C@@H]1CN2CC[C@]3(C(=NC4=C3C(=CC=C4)OC)[C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)O
- InChIKey
- RYENLSMHLCNXJT-CYXFISRXSA-N
- XLogP
- 2.3
- Polar surface area
- 80.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 414.215
Show 5 more facts
- chemical formula
- C₂₃H₃₀N₂O₅
- canonical SMILES
- CCC1CN2CCC3(C(=NC4=C3C(=CC=C4)OC)C2CC1C(=COC)C(=O)OC)O
- isomeric SMILES
- CC[C@@H]1CN2CC[C@]3(C(=NC4=C3C(=CC=C4)OC)[C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)O
- found in taxon
- Mitragyna speciosa
- Commons category
- 7-Hydroxymitragynine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
8 sectionsContents
- Pharmacology
- Synthesis
- Society and culture
- Legal status
- United States
- Research
- See also
- References
7-Hydroxymitragynine (7-OH-MIT, often simply referred to as 7-OH) is a terpenoid indole alkaloid present in the plant Mitragyna speciosa (the leaves of which are commonly known as kratom). It was first described in 1994. In humans, it is produced as an active metabolite of mitragynine via hepatic oxidation.
7-OH exhibits greater binding affinity to μ-opioid receptors (MOR) than mitragynine. It acts primarily as a partial agonist at μ-opioid receptors while antagonizing δ- and κ-opioid receptors; unlike traditional opioids, it appears not to recruit the β-arrestin pathway, which may influence its side effect profile.
Excerpted from Wikipedia’s “7-hydroxymitragynine” article, available under the CC BY-SA 4.0 licence.