(-)-LUPININE Chemical Properties

Melting point:

62-65°C

Boiling point:

160-164°C 4mm

alpha 

D26 -25.9° (c = 3 in water); D28 -21° (c = 9.5 in alcohol)

Density 

0.9660 (rough estimate)

refractive index 

1.4610 (estimate)

Flash point:

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)

color 

Light yellow to yellow

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 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

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(-)-LUPININE Usage And Synthesis

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]¹⁷_D - 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

antifeedant, antiinflammatory, oxytoxic

Uses

(-)-Lupinine is an alkaloid capable of counteracting ethanol anesthesia.

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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