(-)-LUPININE

(-)-LUPININE Basic information
Product Name:(-)-LUPININE
Synonyms:(1R-TRANS)-OCTAHYDRO-2H-QUINOLIZINE-1-METHANOL;(1R,9AR)-1-(OCTAHYDRO-QUINOLIZIN-1-YL)-METHANOL;(1R,9AR)-OCTAHYDRO-2H-QUINOLIZIN-1-YLMETHANOL;2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-;(-)-Lupinine,97%;LUPININE HCL(P);[1R,9aβ,(-)]-Octahydro-2H-quinolizine-1α-methanol;OCTAHYDRO-1H-QUINOLIZIN-1-METHANOL
CAS:486-70-4
MF:C10H19NO
MW:169.26
EINECS:207-638-0
Product Categories:plantgrowth;Alkaloids
Mol File:486-70-4.mol
(-)-LUPININE Structure
(-)-LUPININE Chemical Properties
Melting point 62-65°C
alpha D26 -25.9° (c = 3 in water); D28 -21° (c = 9.5 in alcohol)
Boiling point 160-164°C 4mm
density 0.9660 (rough estimate)
refractive index 1.4610 (estimate)
Fp 160-164°C/4mm
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
form Very Dark Orange
pka14.90±0.10(Predicted)
Merck 14,5609
BRN 80447
Stability:Hygroscopic
LogP1.290 (est)
CAS DataBase Reference486-70-4(CAS DataBase Reference)
NIST Chemistry Reference2H-quinolizine-1-methanol, octahydro-, (1r-trans)-(486-70-4)
Safety Information
Hazard Codes Xi
Risk Statements 20/21/22-41
Safety Statements 22-36/37-39-26
RIDADR 1544
RTECS OK5802000
Hazard Note Irritant
HazardClass 6.1
PackingGroup III
MSDS Information
ProviderLanguage
ALFA English
(-)-LUPININE Usage And Synthesis
DescriptionThis lupin alkaloid was first obtained by Baumert and is present in numerous plants of the Lupinus family, the most important sources being L. luteus, L. niger and L. palmeri Wats. It crystallizes from light petroleum in colourless rhombs and may be boiled without decomposition in a stream of hydrogen. It is laevorotatory with [α]17D - 20.35° (EtOH) and is soluble in H20 and most organic solvents but only sparingly so in petroleum ether. It is a sufficiently strong base to liberate ammonia from its salts. The hydrochloride forms colourless rhombic crystals from aqueous EtOH, m.p. 2l2-3°C; [α]D - 14° (H20); the hydriodide has m.p. 140-1 DC; aurichloride, m.p. 211-3°C; platinichloride as yellow crystals, m.p. 166-166.5°C; (+)-tartrate, m.p. 171°C; [α]D + 15.5° (EtOH); methochloride, m.p. 212-3°C; methiodide, m.p. 295-6°C; phenylurethane, m.p. 98-9°C; (-)-camphorsulphonate, m.p. 184°C; [α]D - 15.3° and the (+)-camphorsulphonate, m.p. 182-3°C; [α]D + 22.5°. The formation of a benzoyl derivative, m.p. 49-S00 C, oxidation of the alkaloid to lupininic acid, C9H16.COOH, m.p. 255°C and dehydration to anhydrolupinine, ClOH17N, a colourless oil of unpleasant odour, b.p. 216-7°C/726 mm all show the presence of a primary alcoholic hydroxyl group. Lupinine does not contain a methylimino group and behaves as a tertiary base. On exhaustive methylation it gives, in three stages, trimethylamine and an unsaturated alcohol. From this, it may be deduced that the alkaloid contains a bicyc1ic system. Several unsuccessful attempts were made to synthesize the alkaloid before this was finally achieved by Clemo and his co-workers.
This alkaloid, like the others of the lupinane group, is of little importance in medicine although the p-aminobenzoate has been shown to possess a marked local anaesthetic action.
The (+ )-form of the alkaloid has m.p. 68°C; [α]D + 19.9° and yields the (-)- tartrate, m.p.167-8°C; [α]D -15.8°.

Chemical PropertiesCrystalline solid, obtained as orthorhombic prisms from acetone; melts at 69°C(156.2°F); bp 270°C (518°F); strongly basic;soluble in water and organic solvents.
UsesThe ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited.
Usesantifeedant, antiinflammatory, oxytoxic
Uses(-)-Lupinine is an alkaloid capable of counteracting ethanol anesthesia.
DefinitionChEBI: Lupinine is a quinolizidine alkaloid.
Health HazardThis alkaloid is moderately toxic. The toxicaction, however, is lower than that of cytisine. Ingestion of high doses may producenausea, convulsions, and respiratory fail ure. The lethal dose in guinea pigs by theintraperitoneal route is 28 mg/kg..
ReferencesBaumert., Ber., 14, 1150, 1321, 1880, 1882 (1881)
Baumert., ibid, 15,631,1951 (1882)
Schmidt, Berend., Arch. Pharm., 235,263 (1897)
Willstiitter, Fourneau., Ber., 35, 1914 (1902)
Karrer et al., Helv. Chirn. Acta, 11, 1062 (1928)
Clemo, Raper, J. Chern. Soc., 1927 (1929)
Winterfeldt, Cosel., Arch. Pharrn., 70, 278 (1940)
Sadykov, Spasokukotski., J. Gen. Chern. USSR, 13,830 (1943)
Sadykov., ibid, 19,143 (1949)
Zaboev., ibid, 18,194 (1948)
Ratusky, Sorm., Chern. Listy., 47, 1491 (1953)







(-)-LUPININE Preparation Products And Raw materials
lupanine L-17-HYDROXYLUPANINE PERCHLORATE LUPININE(REAGENT / STANDARD GRADE) Lupinine acrylate lupinine hydrochloride 4-Lupinine LUPININ HYDROCHLORIDE,LUPININE HCL (-)-LUPININE AKOS NCG-0045 LUPININE(P) Lupinine o-methylbenzoicacid ester hydrochloride ignavine LUPININE(RG) AKOS NCG1-0072 2-Lupinine SULFURIC ACID MONO-[(1R,9AR)-1-(OCTAHYDRO-QUINOLIZIN-1-YL)METHYL] ESTER Lupinine p-chlorobenzoicacid ester hydrochloride

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