| Identification | More | [Name]
(-)-LUPININE | [CAS]
486-70-4 | [Synonyms]
(1R,9AR)-1-(OCTAHYDRO-QUINOLIZIN-1-YL)-METHANOL
(1R,9AR)-OCTAHYDRO-2H-QUINOLIZIN-1-YLMETHANOL
(1R-TRANS)-OCTAHYDRO-2H-QUINOLIZINE-1-METHANOL
LUPININ
(-)-LUPININE
LUPININE
OCTAHYDRO-1H-QUINOLIZIN-1-METHANOL
2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-
(-)-Lupinine,97%
LUPININE HCL(P)
[1R,9aβ,(-)]-Octahydro-2H-quinolizine-1α-methanol | [EINECS(EC#)]
207-638-0 | [Molecular Formula]
C10H19NO | [MDL Number]
MFCD00213431 | [Molecular Weight]
169.26 | [MOL File]
486-70-4.mol |
| Chemical Properties | Back Directory | [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 | [pka]
14.90±0.10(Predicted) | [Merck ]
14,5609 | [BRN ]
80447 | [Stability:]
Hygroscopic | [LogP]
1.290 (est) | [CAS DataBase Reference]
486-70-4(CAS DataBase Reference) | [NIST Chemistry Reference]
2H-quinolizine-1-methanol, octahydro-, (1r-trans)-(486-70-4) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
1544 | [RTECS ]
OK5802000 | [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III |
| Hazard Information | Back Directory | [Description]
This 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 Properties]
Crystalline 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. | [Uses]
(-)-Lupinine is an alkaloid capable of counteracting ethanol anesthesia. | [Uses]
antifeedant, antiinflammatory, oxytoxic | [Uses]
The ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited. | [Definition]
ChEBI: Lupinine is a quinolizidine alkaloid. | [Health Hazard]
This 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.. | [References]
Baumert., 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) |
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