Structure via PubChem · Public domain (PubChem)
(-)-mesembrine
Sign in to saveAlso known as mesembrine
Mesembrine is an alkaloid found within Sceletium tortuosum, commonly known as kanna. This compound is noted for its psychoactive properties, particularly as a serotonin reuptake inhibitor, which contributes to its potential use in treating mood disorders and anxiety. Mesembrine has garnered interest in both traditional medicine and modern pharmacology, where it is explored for its effects on enhancing mood and cognitive function.
Key facts
- Drug.image
- Mesembrine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 160px
- Drug.caption
- Above: molecular structure of mesembrine Below: 3D representation of a mesembrine molecule
- Drug.image2
- Mesembrine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.class
- Serotonin reuptake inhibitor; PDE4 inhibitor
- Drug.ATC_prefix
- None
- Drug.legal_US
- Unscheduled
- Drug.CAS_number
- 468-53-1
- Drug.PubChem
- 394162
- Drug.ChemSpiderID
- 349381
- Drug.UNII
- P5X28MLQ1Z
- Drug.IUPAC_name
- (3aS,7aS)-3a-(3,4-Dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one
- Drug.C
- 17
- Drug.H
- 23
- Drug.N
- 1
- Drug.O
- 3
via Wikipedia infobox
Chemical data
- Formula
- C17H23NO3
- Molecular weight
- 289.4 g/mol
- IUPAC name
- (3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one
- SMILES
- CN1CC[C@]2([C@@H]1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
- InChIKey
- DAHIQPJTGIHDGO-IRXDYDNUSA-N
- XLogP
- 2
- Polar surface area
- 38.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 289.167793596
Show 4 more facts
- isomeric SMILES
- CN1CC[C@]2([C@@H]1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
- chemical formula
- C₁₇H₂₃NO₃
- canonical SMILES
- CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
- Commons category
- Mesembrine
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Pharmacology
- Structure
- Total synthesis
- See also
- References
- Further reading
Mesembrine is an alkaloid found within Sceletium tortuosum, commonly known as kanna. This compound is noted for its psychoactive properties, particularly as a serotonin reuptake inhibitor, which contributes to its potential use in treating mood disorders and anxiety. Mesembrine has garnered interest in both traditional medicine and modern pharmacology, where it is explored for its effects on enhancing mood and cognitive function.
Kanna itself has a long history of use by indigenous peoples in Southern Africa, who utilized it for its mood-enhancing and stress-relieving effects, often consuming it in various forms such as teas or chews.
Excerpted from Wikipedia’s “(-)-mesembrine” article, available under the CC BY-SA 4.0 licence.