Leonurine

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Leonurine
200px
Identifiers
CAS number 24697-74-3 7pxN
PubChem 161464
ChemSpider 141828 7pxY
KEGG C16985 7pxY
Jmol-3D images Image 1
Properties
Molecular formula C14H21N3O5
Molar mass Script error g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 14pxN (verify) (what is: 10pxY/10pxN?)
Infobox references

Leonurine is one of the chemical constituents of the South African plant Leonotis leonurus (Lion's tail). It is a mildly psychoactive alkaloid found in species Leonotis nepetifolia, Leonotis artemisia, Leonurus cardiaca (Motherwort) as well as other plants of family Lamiaceae. Leonurine is easily extracted into water, as well as from the essential oil of Leonurus sibiricus.[1]

Chemical Synthesis

  1. Trimethylgallic acid (Eudesmic acid) is cleaved with 20% sulphuric acid.
  2. Syringic acid is protected with ethylchloroformate.
  3. 4-carboethoxysyringic acid reacted with thionyl chloride SOCl2.
  4. residue reacted with THF yielding 4-carboethoxysyringic acid 4-chloro-1-butyl ester
  5. Gabriel synthesis (Potassium pthalimide) followed by hydrazinolysis (Ing–Manske procedure).
  6. Last step is reaction of the amine with S-Methylisothiourea hemisulfate salt,[2]

yielding 4-Guanidino-1-butanol Syringate.

File:Leonurinesynthesis.svg
Leonurine synthesis.[1]

Traditional uses

Primary uses include treatment of:

References

  1. 1.0 1.1 "The Leonurine and its preparation". An Hui New Star Pharmaceutical Development Co. 2008. Retrieved 2008-08-28. 
  2. "S-Methylisothiourea sulfate structure.". ChemSpider (RSC). 2014. Retrieved 2014-07-09. 

Further reading

      
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