mesembrenone
{{chembox
| ImageFile1 = Mesembrenone2DACS.svg
| ImageSize1 = 150px
| ImageFile2 = Mesembrenone3Dan.gif
| ImageSize2 = 150px
| PIN = (3aR,7aS)-3a-(3,4-Dimethoxyphenyl)-1-methyl-1,2,3,3a,7,7a-hexahydro-6H-indol-6-one
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 468-54-2
| PubChem = 216272
| SMILES = O=C3\C=C/[C@]2(c1ccc(OC)c(OC)c1)[C@@H](N(CC2)C)C3
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID=187467
| 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
| InChIKey = HDNHBCSWFYFPAN-IRXDYDNUSA-N
}}
| Section2 = {{Chembox Properties
| C=17 | H=21 | N = 1 | O=3
| BoilingPt =
| Density =
| MeltingPt=
| Solubility =
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| pKa =
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Mesembrenone is an alkaloid constituent of Sceletium tortuosum (Kanna) and minor constituent of Lampranthus aureus and Lampranthus spectabilis. {{cite journal | doi=10.1076/phbi.36.3.173.6350 | title=The Distribution of Mesembrine Alkaloids in Selected Taxa of the Mesembryanthemaceae and their Modification in the Sceletium Derived 'Kougoed' | year=1998 | last1=Smith | first1=Michael T. | last2=Field | first2=Courtney R. | last3=Crouch | first3=Neil R. | last4=Hirst | first4=Manton | journal=Pharmaceutical Biology | volume=36 | issue=3 | pages=173–179 | doi-access= }}
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).{{ cite journal | author1 = Harvey, A. L. |author2=Young, L. C. |author3=Viljoen, A. M. |author4=Gericke, N. P. | title = Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids | journal = Journal of Ethnopharmacology | volume = 137 | issue = 3 | pages = 1124–1129 |date=October 2011 | pmid = 21798331 | doi = 10.1016/j.jep.2011.07.035 }}
See also
Other alkaloids present in Kanna include:
References
{{Reflist}}
{{Monoamine reuptake inhibitors}}
{{Phosphodiesterase inhibitors}}