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(-)-LUPININE

Product Name
(-)-LUPININE
CAS No.
486-70-4
Chemical Name
(-)-LUPININE
Synonyms
LUPININE;LUPININ;(-)-LUPININE;(-)-LUPININE;(–)-Lupinine;LUPININE HCL(P);(-)-Lupinine,97%;OCTAHYDRO-1H-QUINOLIZIN-1-METHANOL;[(1R,9aR)-quinolizidin-1-yl]methanol;TIANFU-CHEM CAS NO.486-70-4 (-)-LUPININE
CBNumber
CB4409360
Molecular Formula
C10H19NO
Formula Weight
169.26
MOL File
486-70-4.mol
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(-)-LUPININE Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

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N-Bromosuccinimide Price

Alfa Aesar
Product number
L18485
Product name
(-)-Lupinine, 97%
Packaging
500mg
Price
$196.65
Updated
2024/03/01
TRC
Product number
L478018
Product name
(-)-Lupinine
Packaging
10mg
Price
$50
Updated
2021/12/16
Biosynth Carbosynth
Product number
FL61612
Product name
(-)-Lupinine
Packaging
25mg
Price
$80
Updated
2021/12/16
Biosynth Carbosynth
Product number
FL61612
Product name
(-)-Lupinine
Packaging
50mg
Price
$125
Updated
2021/12/16
AK Scientific
Product number
Y9202
Product name
(-)-Lupinine
Packaging
25mg
Price
$158
Updated
2021/12/16
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(-)-LUPININE Chemical Properties,Usage,Production

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

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)

(-)-LUPININE Preparation Products And Raw materials

Raw materials

Preparation Products

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(-)-LUPININE Suppliers

Service Chemical Inc.
Tel
--
Fax
--
Email
sales@chemos-group.com
Country
Germany
ProdList
6350
Advantage
71
ABCR GmbH & CO. KG
Tel
--
Fax
--
Email
info@abcr.de
Country
Germany
ProdList
6831
Advantage
75
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View Lastest Price from (-)-LUPININE manufacturers

Career Henan Chemical Co
Product
(-)-LUPININE 486-70-4
Price
US $1.00/kg
Min. Order
1g
Purity
99%
Supply Ability
100KG
Release date
2018-12-25

486-70-4, (-)-LUPININERelated Search:


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  • (1R,9AR)-1-(OCTAHYDRO-QUINOLIZIN-1-YL)-METHANOL
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  • TIANFU-CHEM CAS NO.486-70-4 (-)-LUPININE
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