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

(-)-Lupinine is a naturally occurring alkaloid that belongs to the lupinane group. It is primarily found in various plants of the Lupinus family, with the most significant sources being L. luteus, L. niger, and L. palmeri Wats. This alkaloid is a crystalline solid, obtained as orthorhombic prisms from acetone, and exhibits strong basic properties. It is soluble in water and most organic solvents, but only sparingly in petroleum ether. (-)-Lupinine is laevorotatory with [α]17D 20.35° (EtOH) and has a melting point of 69°C (156.2°F). It does not contain a methylimino group and behaves as a tertiary base. The alkaloid contains a bicyclic system and has been synthesized successfully by Clemo and his co-workers.

Uses

1. Used in Pharmaceutical Industry:
(-)-Lupinine is used as an antifeedant, which helps in deterring the consumption of certain plants by insects and other pests. This property can be utilized in the development of natural pest control methods and reducing the reliance on synthetic chemicals.
2. Used in Medical Applications:
(-)-Lupinine is used as an anti-inflammatory agent due to its ability to reduce inflammation in the body. This can be beneficial in treating various inflammatory conditions and promoting overall health.
3. Used in Anesthesia:
(-)-Lupinine is an alkaloid capable of counteracting ethanol anesthesia. This property can be useful in medical procedures where ethanol anesthesia is used, as it can help in managing the effects of anesthesia and ensuring patient safety.
4. Used in Research and Development:
The (+)-form of lupinine has a melting point of 68°C and [α]D + 19.9°. It can be used in the synthesis of various derivatives, such as the (-)-tartrate, which has a melting point of 167-8°C and [α]D -15.8°. These derivatives can be further studied for their potential applications in the pharmaceutical and chemical industries.
5. Used in Analytical Chemistry:
(-)-Lupinine can be used as a reference compound in analytical chemistry due to its well-defined chemical properties and strong basic nature. It can be employed in the development of new analytical methods and techniques for the identification and quantification of alkaloids in various samples.

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 
• 16100-91-7 Ethyl (1R,9aR)-Octahydro-2H-quinolizine-1-carboxylate 
• 138713-64-1 (1S,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine 
• 1476-39-7 1,5-diaminopentane dihydrochloride 
• 213884-66-3 (9R,9aR)-9-Hydroxymethyl-1,2,3,8,9,9a-hexahydro-quinolizin-4-one 
• 5176-08-9 1-bromomethylquinolizidine 
• 725250-71-5 (1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester 
• 851183-14-7 (hexahydro-2H-quinolizin-1(6H)-ylidene)methanol 
• 753452-08-3 (3R,4R)-N-allyl-N-[(3-benzoxymethyl)-1,6-heptadien-4-yl]propenamide 
• 753452-09-4 (3S,4S)-N-allyl-N-[(3-benzoxymethyl)-1,6-heptadien-4-yl]propenamide 

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.

Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide

The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by J?rgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner.