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HomeProduct name list(-)-LUPININE

(-)-LUPININE

  • CAS NO.:486-70-4
  • Empirical Formula: C10H19NO
  • Molecular Weight: 169.26
  • MDL number: MFCD00213431
  • EINECS: 207-638-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
(-)-LUPININE Structural

What is (-)-LUPININE?

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.

The Uses of (-)-LUPININE

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

The Uses of (-)-LUPININE

antifeedant, antiinflammatory, oxytoxic

The Uses of (-)-LUPININE

The ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited.

What are the applications of Application

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

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)

Properties of (-)-LUPININE

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
CAS DataBase Reference 486-70-4(CAS DataBase Reference)
NIST Chemistry Reference 2H-quinolizine-1-methanol, octahydro-, (1r-trans)-(486-70-4)

Safety information for (-)-LUPININE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H332:Acute toxicity,inhalation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P321:Specific treatment (see … on this label).
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

Computed Descriptors for (-)-LUPININE

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