Lupinin

Bezeichnung:Lupinin

CAS-Nr486-70-4

Englisch Name:(-)-LUPININE

CBNumberCB4409360

SummenformelC10H19NO

Molgewicht169.26

MOL-Datei486-70-4.mol

Synonyma

Lupinin

Lupinin physikalisch-chemischer Eigenschaften

Schmelzpunkt	62-65°C
Siedepunkt	160-164°C 4mm
alpha	D26 -25.9° (c = 3 in water); D28 -21° (c = 9.5 in alcohol)
Dichte	0.9660 (rough estimate)
Brechungsindex	1.4610 (estimate)
Flammpunkt	160-164°C/4mm
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
Aggregatzustand	Very Dark Orange
pka	14.90±0.10(Predicted)
Merck	14,5609
BRN	80447
Stabilität	Hygroscopic
LogP	1.290 (est)
CAS Datenbank	486-70-4(CAS DataBase Reference)
NIST chemische Informationen	2H-quinolizine-1-methanol, octahydro-, (1r-trans)-(486-70-4)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	20/21/22-41
S-Sätze:	22-36/37-39-26
RIDADR	1544
RTECS-Nr.	OK5802000
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	III

Gefahreninformationscode (GHS)

(-)-LUPININE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
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°.
Chemische Eigenschaften
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.
Verwenden
The ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited.
Verwenden
antifeedant, antiinflammatory, oxytoxic
Verwenden
(-)-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..
Einzelnachweise
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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