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 N

3D model (JSmol)

* Interactive image

ChemSpider |

* 187467 N

PubChem CID

* 216272

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

SMILES

* O=C3\C=C/[C@]2(c1ccc(OC)c(OC)c1)[C@@H](N(CC2)C)C3

Properties

Chemical formula

| C17H21NO3
Molar mass | 287.359 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Mesembrenone is an alkaloid constituent of Sceletium tortuosum (Kanna) and minor constituent of Lampranthus aureus and Lampranthus spectabilis [1]

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; Ki = 27 nM) and also a phosphodiesterase 4 (PDE4) inhibitor (Ki = 470 nM).[2]

## See also

* Mesembrine another alkaloid constituent of Kanna.

## 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.

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*[CID]: Compound ID