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 -25.9^o (C = 3 in water) ; [α]_D²⁸ -21^o (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.