lupinine
2H-quinolizine-1-methanol, octahydro-, (1R-trans)- (9CI)
Identification
| Name | lupinine |
| IUPAC | [(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol |
| CAS Number | 486-70-4 |
| EINECS | 207-638-0 |
| FDA UNII | 33BAJ73U1F |
| Molecular Formula | C10 H19 N O |
| Molecular Weight | 169.26763000 |
| MDL Number | MFCD00213431 |
| Nikkaji Number | J37.652C |
| Beilstein | 0080447 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 70.00 °C. @ 760.00 mm Hg |
| Boiling Point | 270.00 °C. @ 760.00 mm Hg |
| Flash Point | 210.00 °F. TCC ( 99.10 °C. ) (est) |
| logP (o/w) | 1.290 (est) |
| Soluble in | water, 2.512e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intravenous-cat LDLo 100 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LDLo 50 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for lupinine usage levels up to | not for fragrance use. |
| Recommendation for lupinine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(-)-
lupinine
[(1R,9aR)-2,3,4,6,7,8,9,9a-
octahydro-1H-quinolizin-1-yl]methanol
(1R-trans)-
octahydro-2H-quinolizine-1-methanol
2H-
quinolizine-1-methanol, octahydro-, (1R-trans)- (9CI)
PubMed:
Rotational spectra of bicyclic decanes: the trans conformation of (-)-lupinine.
PubMed:
An efficient asymmetric synthesis of (-)-lupinine.
PubMed:
[Isomeric derivatives of lupinine and epilupinine--organophosphorus inhibitors of cholinesterases].
PubMed:
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.
PubMed:
Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline.
PubMed:
Cholinesterase hydrolysis of substituted lupinine benzoates.
PubMed:
[Effect of organophosphorus inhibitors, lupinine and epilupinine derivatives, on mammalian and arthropod cholinesterases].
PubMed:
Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives.
PubMed:
[Synthesis and pharmacokinetic characteristics of 14CH3-polymethacryloyl lupinine--a heparin antagonist].
PubMed:
2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine.
PubMed:
[Antiheparin activity of polymers based on the alkaloid, lupinine].
PubMed:
[Synthesis of lupinine derivatives of flavonoids].
PubMed:
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
PubMed:
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.
PubMed:
[Inhibiting effect of anabasine, anabasamine and lupinine alkaloids on ethanol action in mice].
PubMed:
[Experimental effect of a lupinine-based homopolymer on blood coagulation in animals].
PubMed:
[STUDIES ON THE EFFECT OF PURE LUPININE ALKALOIDS ON THE ANIMAL BODY. THE EFFECT OF LUPININE ON RATS].
PubMed:
A total synthesis of optically active lupinine without benefit of resolution.
PubMed:
[On the knowledge of the rearrangement of lupinine and epilupinine with metallic sodium].
PubMed:
[Cholinesterase substrates based on lupinine and epilupinine].
PubMed:
Synthesis of quinolizine derivatives. 18. Diastereoisomers of 3-(4-chlorobenzyl)quinolizidine, an uterus-contracting agent, and 3-lupinine.
PubMed:
[ON THE BIOSYNTHESIS OF LUPININE].
PubMed:
[BIOSYNTHESIS OF LUPININE ALKALOIDS. 10. THE RELATION BETWEEN DIAMINE OXIDASE AND ALKALOID BIOSYNTHESIS AND ON TETRAHYDROANANBASINE AS A POSSIBLE SYNTHESIS INTERMEDIATE PRODUCT IN LUPINUS LUTEUS].
PubMed:
[The synthesis of 1-carbethoxy- and 3-carbethoxyquinolizidine-2-one, of 1-lupinine and of 1-epilupinine].
PubMed:
Synthesis of quinolizine derivatives. III. Syntheses of 3-aminomethyl- and 3-dimethylaminomethyl-quinolizidine and di-3-lupinine.
PubMed:
The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes.
PubMed:
Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions.
PubMed:
[Reversible lupininin inhibitors of cholinesterases of mammalian blood and of optical ganglia of individuals of the commander squid Berryteuthis magister from different zones of species areal].
PubMed:
A novel sesquiterpene acid and an alkaloid from leaves of the Eastern Nigeria mistletoe, Loranthus micranthus with potent immunostimulatory activity on C57BL6 mice splenocytes and CD69 molecule.
PubMed:
[Derivatives of lupinin and epilupinin as ligands of various cholinesterases].
PubMed:
Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions.
PubMed:
Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition.
PubMed:
Epiquinamide: a poison that wasn't from a frog that was.
PubMed:
[Recent progress on the lupine alkaloids in leguminous plants growing mainly in Japan].
PubMed:
Using the Pummerer cyclization-deprotonation-cycloaddition cascade of imidosulfoxides for alkaloid synthesis.
PubMed:
[The effect of synthetic polycation of the quarternary ammonium salts of polymetacryoil lupinin on the ionic permeability of erythrocyte membrane].
PubMed:
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.
PubMed:
Quinolizidinyl derivatives of 2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid and 1-homolupinanoyl benzimidazolones as ligands for 5-HT3 and 5-HT4 receptors.
PubMed:
Biosynthesis and metabolism of the basic alkaloids.
PubMed:
A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.
PubMed:
Enzyme-linked immunosorbent assay detection of pyrrolizidine alkaloids: immunogens based on quaternary pyrrolizidinium salts.
PubMed:
A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants.
PubMed:
Quinolizidine derivatives with antitubercular activity.
PubMed:
Virgiboidine, A New Alkaloid from Virgilia oroboides and Virgilia divaricata.
PubMed:
Enzymatic synthesis of quinolizidine alkaloid esters: a tigloyl-CoA: 13-hydroxylupanine O-tigloyltransferase from Lupinus albus L.
PubMed:
Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico.
PubMed:
Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.
PubMed:
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.
PubMed:
Indolizidine and quinolizidine alkaloids.
PubMed:
Relative and absolute configuration of aloperine.
PubMed:
[Lupins - a new source of food for Andean countries. 5. Traditional methods of debittering of lupins by water].
PubMed:
An investigation of Sophora secundiflora seeds (Mescalbeans).