Leonurine

Leonurine
Names
	IUPAC name 4-(Diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
Identifiers
CAS Number	24697-74-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	141828 ;
ECHA InfoCard	100.208.686
KEGG	C16985 ;
PubChem CID	161464;
CompTox Dashboard (EPA)	DTXSID70179434 ;
	InChI InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17) Key: WNGSUWLDMZFYNZ-UHFFFAOYSA-N ; InChI=1/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17) Key: WNGSUWLDMZFYNZ-UHFFFAOYAI;
	SMILES O=C(OCCCC/N=C(\N)N)c1cc(OC)c(O)c(OC)c1;
Properties
Chemical formula	C14H21N3O5
Molar mass	311.338 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Leonurine is a pseudoalkaloid that has been isolated from Leonotis leonurus (Lion's tail), Leonotis nepetifolia, Leonotis artemisia, Leonurus cardiaca (Motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae. Leonurine is easily extracted into water.^[1]

Chemical synthesis

Leonurine can be synthesized starting from eudesmic acid. Reaction with sulfuric acid produces syringic acid. Protection with ethyl chloroformate followed by reaction with thionyl chloride SOCl₂ and then tetrahydrofuran yields 4-carboethoxysyringic acid 4-chloro-1-butyl ester. The chloride is then converted to an amino group via a Gabriel synthesis with potassium pthalimide) followed by hydrazinolysis (Ing–Manske procedure). The final step is reaction of the amine with S-methylisothiourea hemisulfate salt.^[2]

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