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Mesembrine

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Title: Mesembrine  
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Subject: Sceletium tortuosum, Total synthesis, BAY 73-6691, Discovery and development of phosphodiesterase 5 inhibitors, Tofisopam
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Mesembrine

Mesembrine
IUPAC name

(3aS,7aS)-3a- (3,4-dimethoxyphenyl)- 1-methyl-2,3,4,5,7,7a- hexahydroindol-6-one

Identifiers
CAS number  N
PubChem
ChemSpider  N
Jmol-3D images Image 1
Properties
Molecular formula C17H23NO3
Molar mass 289.37 g mol−1
log P 1.1
Supplementary data page
Structure and
properties 		n, εr, 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 (77 °F), 100 kPa)
 N   YesY/N?)

Mesembrine is an alkaloid present in Sceletium tortuosum (kanna).[1] It has been shown to act as a serotonin reuptake inhibitor (Ki=1.4nM), and more recently, has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4) (Ki=7,800nM).[2] As such, mesembrine may contribute to the antidepressant effects of kanna.[3] The levorotary isomer, (-)-mesembrine, is the natural form. [4]

References

  1. ^ Smith, M. T.; Crouch, N. R.; Gericke, N.; Hirst, M. (March 1996). "Psychoactive constituents of the genus Sceletium N.E.Br. and other Mesembryanthemaceae: A Review". Journal of Ethnopharmacology 50 (3): 119–130.  
  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.  
  3. ^ Stafford, G. I.; Pedersen, M. E.; van Staden, J.; Jäger, A. K. (October 2008). "Review on plants with CNS-effects used in traditional South African medicine against mental diseases". Journal of Ethnopharmacology 119 (3): 513–537.  
  4. ^ Coggon, P.; Farrier, D.S.; Jeffs, P.W.; McPhail, A.T. (1970). "Absolute configuration of mesembrine and related alkaloids: X-ray analysis of 6-epimesembranol methiodide.". J. Chem. Soc. B: 1267–1271.  
PDE1
PDE2
PDE3
PDE4
PDE5
PDE6
PDE7
PDE9
PDE10
PDE11
Nonselective
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