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Mesembrine

Mesembrine

IUPAC name	(3aS,7aR)-3a- (3,4-dimethoxyphenyl)- 1-methyl-2,3,4,5,7,7a- hexahydroindol-6-one
Identifiers
CAS number	468-53-1
PubChem	193296
SMILES	CN1CC[C@@]2 ([C@H]1CC(=O)CC2) C3=CC(=C(C=C3)OC)OC
Properties
Molecular formula	C₁₇H₂₃NO₃
Molar mass	289.37 g mol^-1
log P	1.1
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Mesembrine is an alkaloid present in Sceletium tortuosum.^[1] It has been shown to be an extremely potent serotonin reuptake inhibitor, active at dosages as low as 100μg (micrograms).^[2] It has also been shown to be a PDE4-inhibitor.^[3] Mesembrine may contribute to the antidepressant effects of kanna.

References

^ Smith M, Crouch N, Gericke N, Hirst M (1996). "Psychoactive constituents of the genus Sceletium N.E.Br. and other Mesembryanthemaceae: a review". J Ethnopharmacol 50 (3): 119–30. PMID 8691846.
^ Pharmaceutical compositions containing mesembrine and related compounds. U.S. Patent 6,288,104 (PDF)
^ Mesembrine - an inhibitor of PDE4 that follows structure-activity relationship to rolipram. [1]

v • d • e Selective Phosphodiesterase inhibitors (C01CE, G04BE)
PDE1	Vinpocetine
PDE2	EHNA
PDE3	Amrinone, Bucladesine, Enoximone, Milrinone
PDE4	HT-0712, Ibudilast, Mesembrine, Rolipram
PDE5	Avanafil, Sildenafil, Tadalafil, Udenafil, Vardenafil