Mesembrenone

Mesembrenone
Names


IUPAC name (3aR,7aS)-3a-(3,4-Dimethoxyphenyl)-1-methyl-1,2,3,3a,7,7a-hexahydro-6H-indol-6-one
Identifiers
CAS Registry Number	468-54-2^N
ChemSpider	187467^N
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/s1 Key: HDNHBCSWFYFPAN-IRXDYDNUSA-N
Jmol-3D images	Image
PubChem	216272
SMILES O=C3\C=C/[C@]2(c1ccc(OC)c(OC)c1)[C@@H](N(CC2)C)C3
Properties
Molecular formula	C₁₇H₂₁NO₃
Molar mass	287.35 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Mesembrenone is an alkaloid constituent of Sceletium tortuosum (Kanna). 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).^[1]

References

↑ 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.