Lupinine

Lupinine
Names
	Preferred IUPAC name [(1R,9aR)-Octahydro-2H-quinolizin-1-yl]methane
Identifiers
CAS Number	486-70-4 ;
3D model (JSmol)	Interactive image;
3DMet	B04202;
ChEBI	CHEBI:28012 ;
ChEMBL	ChEMBL459397 ;
ChemSpider	82587 ;
ECHA InfoCard	100.006.944
EC Number	207-638-0;
KEGG	C10773;
PubChem CID	91461;
UNII	33BAJ73U1F;
CompTox Dashboard (EPA)	DTXSID00197565;
	InChI InChI=1S/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1 Key: HDVAWXXJVMJBAR-VHSXEESVSA-N ; InChI=1/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1 Key: HDVAWXXJVMJBAR-VHSXEESVBK;
	SMILES OC[C@H]1[C@@H]2N(CCC1)CCCC2;
Properties
Chemical formula	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)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	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). verify (what is ?) Infobox references

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 :5 was invoked but never defined (see the help page).
^ Cite error: The named reference :10 was 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.

[1] 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.

[:5-2] Cite error: The named reference :5 was invoked but never defined (see the help page).

[:10-3] Cite error: The named reference :10 was invoked but never defined (see the help page).

[:4-4] 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.

[:8-5] 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)

[6] 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.

[:7-7] Róbertsdóttir, Anna Rósa (2016). Icelandic herbs and their medicinal uses. Berkeley, California. ISBN 9781623170226. OCLC 910979700.{{cite book}}: CS1 maint: location missing publisher (link)

[8] 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.

[:3-9] 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)

[10] 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.

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