Home Categories Natural Products ((1R,9aR)-Octahydro-1H-quinolizin-1-yl)methanol
BD0852748

((1R,9aR)-Octahydro-1H-quinolizin-1-yl)methanol , 95% , 486-70-4

CAS NO.:486-70-4

Empirical Formula: C10H19NO

Molecular Weight: 169.26

MDL number: MFCD00213431

EINECS: 207-638-0

Pack Size Price Stock Quantity
100mg RMB219.20 In Stock
250mg RMB372.00 In Stock
1g RMB1002.40 In Stock
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Update time: 2022-07-08

PRODUCT 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)

Description and Uses

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°.

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

Safety

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H312-H332
Precautionary statements  P261-P280h-P301+P312a-P304+P340-P321-P501a
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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