Lupinine-Synonyms l-Lupinine; (–)-Lupinine-obtained from the seeds and herb of Lupinus luteus , Anabasis aphylla

A. Lupinine

Synonyms l-Lupinine; (–)-Lupinine.
Biological Source The naturally occurring l-form is obtained from the seeds and herb of Lupinus luteus L. and other Lupinus species belonging to the natural order Lequminoseae; and also found in Anabasis aphylla L. (Chenopodiaceae).
Chemical Structure

[1R-trans]-Octahydro-2H-quinolizidine-1-methanol (C10H19NO).
Isolation The isolation of lupinine from the seeds and herb of Lupinus lutens may be affected by the method evolved by Couch* (1934).
Characteristic Features
1. Lupinine is obtained as stout orthorhombic prisms from acetone having mp 68.5-69.2°C.
2. Its physical parameters are: bp4 160-164°C; bp755 269-270°C; [α]D26 -25.9o (C = 3 in water) ; [α]D28 -21o (C = 9.5 in ethanol);
3. It is soluble in water, ethanol, ether and chloroform.
4. It is a strong base.
Identification Tests
1. l-Form Lupinine Hydrochloride Derivative (C10H20ClNO): Its orthorhombic prisms have mp 208-213°C, and [α]D –14°.
2. dl-Form Lupinine: The crystals obtained from acetone have mp 58.5-59.5°C.

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