Global InformationLupinine information
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| Preferred IUPAC name
[(1R,9aR)-Octahydro-2H-quinolizin-1-yl]methane | |
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3D model (JSmol)
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| ECHA InfoCard | 100.006.944 |
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CompTox Dashboard (EPA)
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| Properties | |
Chemical formula
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C10H19NO |
| Molar mass | 169.268 g·mol−1 |
| Melting point | 68 to 69 °C (154 to 156 °F; 341 to 342 K) |
| Boiling point | 269 to 270 °C (516 to 518 °F; 542 to 543 K) |
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Pictograms
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Signal word
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Warning |
Hazard statements
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H302, H312, H332 |
Precautionary statements
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P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Lupinine is a quinolizidine alkaloid present in the genus Lupinus (colloquially referred to as lupins) of the flowering plant family Fabaceae.[1] The scientific literature contains many reports on the isolation and synthesis of this compound as well as a vast number of studies on its biosynthesis from its natural precursor, lysine.[2][3] Studies have shown that lupinine hydrochloride is a mildly toxic acetylcholinesterase inhibitor and that lupinine has an inhibitory effect on acetylcholine receptors.[4][5] The characteristically bitter taste of lupin beans, which come from the seeds of Lupinus plants, is attributable to the quinolizidine alkaloids which they contain, rendering them unsuitable for human and animal consumption unless handled properly.[6][7] However, because lupin beans have potential nutritional value due to their high protein content,[8] efforts have been made to reduce their alkaloid content through the development of "sweet" varieties of Lupinus.[9][10]
- ^ Wink, Michael; Meißner, Carsten; Witte, Ludger (January 1995). "Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus". Phytochemistry. 38 (1): 139–153. Bibcode:1995PChem..38..139W. doi:10.1016/0031-9422(95)91890-d. ISSN 0031-9422.
- ^ Cite error: The named reference
:5was invoked but never defined (see the help page). - ^ Cite error: The named reference
:10was invoked but never defined (see the help page). - ^ Rozengart, E. V.; Basova, N. E. (2001-11-01). "Ammonium Compounds with Localized and Delocalized Charge as Reversible Inhibitors of Cholinesterases of Different Origin". Journal of Evolutionary Biochemistry and Physiology. 37 (6): 604–610. doi:10.1023/A:1014414126143. ISSN 0022-0930. S2CID 25689578.
- ^ Risikobewertung, Bundesinstitut Für (2017). "Risk assessment of the occurrence of alkaloids in lupin seeds" (PDF). OpenAgrar. doi:10.17590/20170530-142504.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Bleitgen, R.; Gross, R.; Gross, U. (1979-06-01). "Die Lupine — ein Beitrag zur Nahrungsversorgung in den Anden". Zeitschrift für Ernährungswissenschaft (in German). 18 (2): 104–111. doi:10.1007/BF02023724. ISSN 0044-264X. PMID 556411. S2CID 82321535.
- ^ Róbertsdóttir, Anna Rósa (2016). Icelandic herbs and their medicinal uses. Berkeley, California. ISBN 9781623170226. OCLC 910979700.
{{cite book}}: CS1 maint: location missing publisher (link) - ^ Yáñez, Enrique; Ivanović, D.; Owen, D.F.; Ballester, D. (1983). "Chemical and Nutritional Evaluation of Sweet Lupines". Annals of Nutrition and Metabolism. 27 (6): 513–520. doi:10.1159/000176728. ISSN 1421-9697. PMID 6651228.
- ^ Introduction to neurobehavioral toxicology : food and environment. Niesink, Raymundus Johannes Maria, 1953-. Boca Raton: CRC Press. 1999. ISBN 978-0849378027. OCLC 39764034.
{{cite book}}: CS1 maint: others (link) - ^ Torres Tello, F.; Nagata, A.; Dreifuss Spiegel, W. (June 1980). "[Methods of eliminating alkaloids from the seeds of Lupinus mutabilis Sweet]". Archivos Latinoamericanos de Nutricion. 30 (2): 200–209. ISSN 0004-0622. PMID 7212919.