486-70-4

Basic information

• Product Name: (-)-LUPININE
• Synonyms: (1R-TRANS)-OCTAHYDRO-2H-QUINOLIZINE-1-METHANOL;(1R,9AR)-1-(OCTAHYDRO-QUINOLIZIN-1-YL)-METHANOL;(1R,9AR)-OCTAHYDRO-2H-QUINOLIZIN-1-YLMETHANOL;2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-;(-)-Lupinine,97%;LUPININE HCL(P);[1R,9aβ,(-)]-Octahydro-2H-quinolizine-1α-methanol;[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
• CAS NO: 486-70-4
• Molecular Formula: C₁₀H₁₉NO
• Molecular Weight: 169.26
• EINECS: 207-638-0
• Product Categories: Alkaloids;plantgrowth
• Mol File: 486-70-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 62-65°C
• Boiling Point: 160-164°C 4mm
• Flash Point: 160-164°C/4mm
• Appearance: /
• Density: 0.9660 (rough estimate)
• Vapor Pressure: 0.000928mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• PKA: 14.90±0.10(Predicted)
• Merck: 14,5609
• BRN: 80447
• CAS DataBase Reference: (-)-LUPININE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-LUPININE(486-70-4)
• EPA Substance Registry System: (-)-LUPININE(486-70-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-41
• Safety Statements: 22-36/37-39-26
• RIDADR: 1544
• RTECS: OK5802000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 486-70-4(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 486-70-4 differently. You can refer to the following data:
1. antifeedant, antiinflammatory, oxytoxic
2. (-)-Lupinine is an alkaloid capable of counteracting ethanol anesthesia.
3. The ι-form of lupinine occurs in seeds andherb of Lupinus luteous L., Chenopodiaceae,and other lupinus species. Its clinical applications are very limited.

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)

InChI:InChI=1/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10-/m1/s1

Upstream product

• 10248-30-3 lupinine 
• 1055874-40-2 ethyl (1R,9aR)-6-oxooctahydro-2H-quinolizine-1-carboxylate 
• 725250-71-5 (1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester 
• 5176-08-9 1-bromomethylquinolizidine 
• 213884-66-3 (9R,9aR)-9-Hydroxymethyl-1,2,3,8,9,9a-hexahydro-quinolizin-4-one 
• 138713-64-1 (1S,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 16100-91-7 Ethyl (1R,9aR)-Octahydro-2H-quinolizine-1-carboxylate 
• 117471-84-8 1,1-dimethylethyl (E)-7-hydroxyhept-2-enoate 
• 1619924-96-7 C₁₄H₂₅NO₂ 
• 1619924-94-5 tert-butyl (R,R)-2-[N(1')-(p-methoxybenzyl)piperidin-2'-yl]-5-hydroxypentanoate 
• 1619924-93-4 tert-butyl (R,R)-2-[N(1')-(p-methoxybenzyl)piperidin-2'-yl]-5-(tert-butyldimethylsiloxy)pentanoate 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 1619924-92-3 tert-butyl (R)-2-[N(1')-(p-methoxybenzyl)piperidin-2'-yl]acetate 
• 1619924-90-1 tert-butyl (R,R)-3-[N-(p-methoxybenzyl)-N-(α-methyl-p-methoxybenzyl)amino]-7-chloroheptanoate 

Downstream Products

• 40179-92-8 O-benzoyl-(-)-lupinine 
• 6113-14-0 phenylurethane of (-)-lupinin 
• 38734-34-8 4-nitro-benzoic acid-((9aR)-(9ar)-octahydroquinolizin-1t-ylmethyl ester) 
• 5280-36-4 (9aR)-1t-(toluene-4-sulfonyloxymethyl)-(9ar)-octahydro-quinolizin 
• 486-71-5 (+)-epilupinine 
• 574-99-2 (1R,9aR)-octahydro-1H-quinolizine-1-carboxylic acid 
• 139403-39-7 O-cinnamoyllupinine 
• 362495-17-8 4-Chloro-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester 
• 68676-73-3 4-Nitro-N-[(1S,9aR)-1-(octahydro-quinolizin-1-yl)methyl]-benzamide 

Relevant articles and documents

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Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline

Recently the N-(-)-lupinyl-derivative of 7-chloro-4-aminoquinoline ((-)-AM-1; 7-chloro-4-{N-[(1S,9aR)(octahydro-2H-quinolizin-1-yl)methyl]amino} quinoline) showed potent in vitro and in vivo activity against both Chloroquine susceptible and resistant strains of Plasmodium falciparum. However, (-)-AM-1 is synthesized starting from (-)-lupinine, an expensive alkaloid isolated from Lupinus luteus whose worldwide production is not sufficient, at present, for large market purposes. To overcome this issue, the corresponding racemic compound, derived from synthetic (±)-lupinine was considered a cheaper alternative for the development of a novel antimalarial agent. Therefore, the racemic and the 7-chloro-4-(N-(+)-lupinyl)aminoquinoline ((±)-AM-1; (+)-AM-1) were synthesized and their in vitro antimalarial activity and cytotoxicity compared with those of (-)-AM-1. The (+)-lupinine required for the synthesis of (+)-AM-1 was obtained through a not previously described lipase catalyzed kinetic resolution of (±)-lupinine. In terms of antimalarial activity, (±)-AM1 and (+)-AM1 demonstrated very good activity in vitro against both CQ-R and CQ-S strains of P. falciparum (range IC50 16-35 nM), and low toxicity against human normal cell lines (therapeutic index >1000), comparable with that of (-)-AM1. These results confirm that the racemate (±)-AM1 could be considered as a potential antimalarial agent, ensuring a decrease of costs of synthesis compared to (-)-AM1.

Short total synthesis of (-)-lupinine and (-)-epiquinamide by double Mitsunobu reaction

Alternative total syntheses of (-)-lupinine (1) and (-)-epiquinamide (2) have been described via the key intermediate 3 obtained from the addition of 2-trialkylsilyloxyfuran 5 to N-acyliminium intermediate derived from 4. The major R,R-isomer 8 obtained from the Mannich reaction was converted into its R,S-isomer through Mitsunobu reaction. Then, a second Mitsunobu reaction of 3 led to cyano 9 and azido 11 derivatives, which were converted into 1 and 2 in 33 and 36% overall yield from 4, respectively. The synthetic route is amenable for the generation of several quinolizidine alkaloids. Georg Thieme Verlag Stuttgart · New York.