Lupanine-Biological Source It is obtained from the herb of Genista tinctoria L. (Fabaceae) (Dyer’s Broom)

B. Lupanine


Biological Source It is obtained from the herb of Genista tinctoria L. (Fabaceae) (Dyer’s Broom).
Chemical Structure

Lupanine
(7α, 7aα, 14α, 14aβ)-Dodecahydro-7, 14-methano-2H, 11H-dipyridiol [1, 2-a: 1’, 2’-e] diazocin-11-one; (C15H24N2O].
Isolation The racemic and optical isomers of lupanine have been duly isolated from various species of Lupinus (Fabaceae/Leguminosae) as stated below:
(±)-Lupanine—from white lupins;
d-Lupanine—from blue lupins;
l-Lupanine—from the natural racemic form;
Characteristic Features The physical parameters of the above three forms of lupanine are given below:
dl-Lupanine: It is obtained as orthorhombic prisms obtained from acetone having mp 98-99°C; bp1.0 185-195°C; It is soluble in ethanol, ether, chloroform and water; and insoluble in petroleum ether.
d-Lupanine (Synonym: 2-Oxosparteine): It is obtained as syrup crystallizing difficultly in hygroscopic needles having mp 40-44°C; bp3 190-193°C; nD24 1.5444; [α]D25  +84o (C = 4.8 in ethanol). It is found to be freely soluble in water, ethanol, ether and chloroform.
l-Lupanine (Synonym: Hydrorhombinine): It is a viscous liquid having bp1.0 186-188°C; [α]D - 61o in acetone.
Identification Test Lupanine forms the corresponding lupanine hydrochloride dihydrate (C15H24N2O.HCl.2H2O) which is obtained as rhombic crystals from water having mp 127°C (dry).
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* Couch, J.F., J. Am. Chem. Soc., 56, 2434 (1934).

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