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Mesembrenone

Names
Preferred IUPAC name (3aR,7aS)-3a-(3,4-Dimethoxyphenyl)-1-methyl-1,2,3,3a,7,7a-hexahydro-6H-indol-6-one
Identifiers
CAS Number	468-54-2
3D model (JSmol)	Interactive image
ChemSpider	187467
PubChem CID	216272
CompTox Dashboard (EPA)	DTXSID60963667
InChI InChI=1S/C17H21NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-7,10,16H,8-9,11H2,1-3H3/t16-,17-/m0/s1Key: HDNHBCSWFYFPAN-IRXDYDNUSA-N
SMILES O=C3\C=C/2(c1ccc(OC)c(OC)c1)(N(CC2)C)C3
Properties
Chemical formula	C17H21NO3
Molar mass	287.359 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Mesembrenone is an alkaloid constituent of Sceletium tortuosum (Kanna) and minor constituent of Lampranthus aureus and Lampranthus spectabilis.

Similar to modern synthetic antidepressants, it is a potent (IC₅₀ < 1 μM) selective inhibitor of the serotonin transporter (SERT) (that is, a selective serotonin reuptake inhibitor; K_i = 27 nM) and also a phosphodiesterase 4 (PDE4) inhibitor (K_i = 470 nM).

See also

Other alkaloids present in Kanna include:

• Mesembrine
• Mesembranol
• Tortuosamine

References

1. Smith, Michael T.; Field, Courtney R.; Crouch, Neil R.; Hirst, Manton (1998). "The Distribution of Mesembrine Alkaloids in Selected Taxa of the Mesembryanthemaceae and their Modification in the Sceletium Derived 'Kougoed'". Pharmaceutical Biology. 36 (3): 173–179. doi:10.1076/phbi.36.3.173.6350.
2. Harvey, A. L.; Young, L. C.; Viljoen, A. M.; Gericke, N. P. (October 2011). "Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids". Journal of Ethnopharmacology. 137 (3): 1124–1129. doi:10.1016/j.jep.2011.07.035. PMID 21798331.

• Antidepressants
• Indole alkaloids
• Ketones
• Monoamine releasing agents
• Phenol ethers
• PDE4 inhibitors
• Serotonin reuptake inhibitors