Lupinine (10248-30-3, 486-70-4)

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Suppliers

• Sigma-Aldrich - Lupinine
  75.00 - 128.75 USD
• Fisher Scientific - Search for Lupinine
• TCI - Search for Lupinine

Most-cited Publications

• Syntheses of isoretronecanol and lupinine (Journal of Organic Chemistry, 1982)
• Quinolizidine alkaloid synthesis via the intramolecular imino Diels-Alder reaction. Epi-lupinine and cryptopleurine (Journal of Organic Chemistry, 1983)
• Conversion of N-acyl-2,3-dihydro-4-pyridones to 4-chloro-1,2-dihydropyridines using the Vilsmeier reagent. Synthesis of (-)-coniine and ()-lupinine (Journal of Organic Chemistry, 1993)
• Double RingClosing Metathesis Reaction of NitrogenContaining Tetraenes: Efficient Construction of Bicyclic Alkaloid Skeletons and Synthetic Application to Four Stereoisomers of Lupinine and Their Derivatives (Chemistry: A European Journal, 2004)
• Quinolizidine synthesis via intramolecular immonium ion based Diels-Alder reactions. Total synthesis of (.+-.)-lupinine, (.+-.)-epilupinine, (.+-.)-cryptopleurine, and (.+-.)-julandine (Journal of Organic Chemistry, 1988)
• The Relative Toxicity of Nicotine, Anabasine, Methyl Anabasine, and Lupinine for Culicine Mosquito Larvae (Journal of Economic Entomology, 1933)

Areas of Application

Safety

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Trends

Alternate Names

• lupinine hydrochloride, (1R-trans)-isomer
• 1S-cis-octahydro-2H-quinolizine-1-methanol
• lupinine, (1S-cis)-isomer
• epilupinine
• SMILES
  C1CCN2CCCC(C2C1)CO
• InChIKey
  HDVAWXXJVMJBAR-UHFFFAOYSA-N

External Links

• Pubchem - Lupinine
• Wikipedia - lupinine
  Lupinine is a bitter tasting quinolizidine alkaloid present in Lupinus species (lupins), plants of the family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound. The characteristically bitter taste of lupin beans, attributable to the alkaloids which they contain, renders them unsuitable for human and animal consumption.

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Lupinine

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