Mesembrenone

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
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/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

Mesembrenone is an alkaloid found in Sceletium tortuosum (Kanna) and minor constituent of Lampranthus aureus and Lampranthus spectabilis.^[1] Mesembrenone is a MAO-B inhibitor, that means it blocks the enzyme that breaks down dopamine in the brain resulting in increased dopamine levels when consumed, either orally, smoked, or snorted.

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).^[2]