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Mesembrine

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Mesembrine
File:Mesembrine2DACS2.svg
Names
IUPAC name
(3aS,7aS)-3a- (3,4-dimethoxyphenyl)- 1-methyl-2,3,4,5,7,7a- hexahydroindol-6-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m1/s1 checkY
    Key: DAHIQPJTGIHDGO-IAGOWNOFSA-N checkY
  • InChI=1/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m1/s1
    Key: DAHIQPJTGIHDGO-IAGOWNOFBH
  • CN1CC[C@@]2([C@H]1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
Properties
289.37
Molar mass 289.375 g·mol−1
log P 1.1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒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]

Rat studies have evaluated effects of kanna extract, finding analgesic and antidepressant potential.[5] No adverse results were noted for a commercial extract up to 5000 mg/kg daily.[6]

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. doi:10.1016/0378-8741(95)01342-3. PMID 8691846.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. doi:10.1016/j.jep.2008.08.010. PMID 18775771.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. doi:10.1039/J29700001267.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ "Effects of Sceletium tortuosum in rats". J Ethnopharmacol. 155: 731–5. Aug 8, 2014. doi:10.1016/j.jep.2014.06.007. PMID 24930358.
  6. ^ "A toxicological safety assessment of a standardized extract of Sceletium tortuosum (Zembrin(®)) in rats". Food Chem Toxicol. 74: 190–9. Dec 2014. doi:10.1016/j.fct.2014.09.017. PMID 25301237.
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