2H-quinolizine-1-methanol, octahydro-, (1R-trans)- (9CI)

CAS: 486-70-4 C10 H19 N O MW: 169.26763000

Identification

Namelupinine
IUPAC[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
CAS Number486-70-4
EINECS207-638-0
FDA UNII33BAJ73U1F
Molecular FormulaC10 H19 N O
Molecular Weight169.26763000
MDL NumberMFCD00213431
Nikkaji NumberJ37.652C
Beilstein0080447

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 SDSView
Oral/Parenteral Toxicityintravenous-cat LDLo 100 mg/kg
Dermal Toxicitysubcutaneous-mouse LDLo 50 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for lupinine usage levels up tonot for fragrance use.
Recommendation for lupinine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

anabisis aphylla

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).