486-87-3

Basic information

• Product Name: (+)-alpha-isolupanine
• Synonyms: (+)-alpha-isolupanine;(+)-11-Isolupanine;[7S,(+)]-1,2,3,7,7aα,8,9,10,11,13,14,14aα-Dodecahydro-7α,14α-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one;11-Isolupanine;Isolupanine;α-Isolupanin;α-Isolupanine;7,11-Methano-4H,6H-dipyrido(1,2-A:1',2'-E)(1,5)diazocin-4-one, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14aalpha))-
• CAS NO: 486-87-3
• Molecular Formula: C₁₅H₂₄N₂O
• Molecular Weight: 248.36386
• EINECS: 207-644-3
• Product Categories: Alkaloids
• Mol File: 486-87-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 75-76°
• Boiling Point: 396.7°Cat760mmHg
• Flash Point: 172.7°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 1.67E-06mmHg at 25°C
• Refractive Index: 1.581
• PKA: 9.47±0.20(Predicted)
• CAS DataBase Reference: (+)-alpha-isolupanine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-alpha-isolupanine(486-87-3)
• EPA Substance Registry System: (+)-alpha-isolupanine(486-87-3)

Safety Data

• Hazardous Substances Data: 486-87-3(Hazardous Substances Data)

Usage

General Description

(+)-alpha-isolupanine is a naturally occurring alkaloid compound found in various plants, including members of the Solanaceae and Leguminosae families. It is a stereoisomer of alpha-isolupanine and has been identified as a precursor in the biosynthesis of nicotine in tobacco plants. The compound has been isolated and studied for its potential pharmaceutical properties, including its role as an acetylcholinesterase inhibitor, which could make it useful in the treatment of neurodegenerative diseases such as Alzheimer's. Additionally, (+)-alpha-isolupanine has been investigated for its potential as an anti-inflammatory and analgesic agent, although further research is needed to fully understand its medicinal potential.

InChI:InChI=1/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2

Upstream product

• 90-39-1 (-)-sparteine 
• 6940-78-9 4-chlorobutyl bromide 
• 64-19-7 acetic acid 
• 35611-60-0 11,12-dehydrolupanine 
• 64-17-5 ethanol 
• 1476-39-7 1,5-diaminopentane dihydrochloride 

Downstream Products

• 106656-92-2 2-(p-tolyl)-2-dehydrosparteine 

Relevant articles and documents

The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach

Bisquinolizidine alkaloids are characterized by a chiral bispidine core (3,7-diazabicyclo[3.3.1]nonane) to which combinations of an α,N-fused 2-pyridone, an endo- or exo-α,N-annulated piperidin(on)e, and an exo-allyl substituent are attached. We developed a modular “inside-out” approach that permits access to most members of this class. Its applicability was proven in the asymmetric synthesis of 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses. Key steps are the first successful preparation of both enantiomers of C2-symmetric 2,6-dioxobispidine by desymmetrization of a 2,4,6,8-tetraoxo precursor, the construction of the α,N-fused 2-pyridone by using an enamine-bromoacrylic acid strategy, and the installation of endo- or, optionally, exo-annulated piperidin(on)es.

Synthesis of Cadaverine and its Incorporation into five Quinolizidine Alkaloids

Cadaverine dihydrochloride (13) was synthesised by the sequential introduction of two equivalents of sodium cyanide to a C3 precursor, and it was fed to Lupinus luteus and L. polyphyllus plants.Complete labelling patterns were obtained in five quinolizidine alkaloids by 13C n.m.r. spectroscopy.The 13C-13C doublets observed in the spectra of (-)-lupinine (3), (-)-sparteine (4), (+)-lupanine (5), (+)-13α-hydroxylupanine (6), and (+)-angustifoline (7) derived biosynthetically from the doubly labelled precursor (13) confirm the intact, specific incorporation of two cadaverine units into the tetracyclic quinolizidine alkaloid skeletons.The cadaverine (13) units are incorporated to about the same extent into each part of the quinolizidine alkaloids (3)-(7).Two of the 13C chemical shifts for lupanine (5) have been reassigned.The labelling pattern of the tricyclic alkaloid angustifoline (7) indicates that the allyl group originates by degradation of one ring of a tetracyclic precursor.