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(+)-Lupanine

(+)-Lupanine structure

(+)-Lupanine 

structure
  • CAS No:

    550-90-3

  • Formula:

    C15H24N2O

  • Chemical Name:

    (+)-Lupanine

  • Synonyms:

    7,14-Methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one,dodecahydro-,(7S,7aR,14S,14aS)-;Lupanine;7,14-Methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one,dodecahydro-,[7S-(7α,7aα,14α,14aβ)]-;Lupanine,d-;(7S,7aR,14S,14aS)-Dodecahydro-7,14-methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one;Lupanin;2-Oxosparteine;(+)-Lupanine;7,14-Methano-4H,6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-4-one,dodecahydro-,[7S-(7α,7aβ,14α,14aα)]-;d-Lupanine;(+)-2-Oxosparteine;D-(+)-Lupanine;D-Lupanine;1617-54-5;15043-15-9

  • Categories:

    Natural Products  >  Alkaloids

Description

ChEBI: The delta-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyc ic quinolizidine alkaloids.


Lupanine is the delta-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyclic quinolizidine alkaloids. It is a quinolizidine alkaloid, a tertiary amine and a delta-lactam. It is a conjugate base of a lupanine(1+). It derives from a hydride of a sparteine.

(+)-Lupanine Basic Attributes

248.368

248.36

183KU7535A

Characteristics

23.55000

13.33

0.9±0.1 g/cm3

99 °C

186-188 °C @ Press: 1 Torr

221.8±13.1 °C

1.498

D25 +84° (c = 4.8 in alc)

Drug Information

alpha-isolupanine

Computed Properties

Molecular Weight:248.36
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Exact Mass:248.188863393
Monoisotopic Mass:248.188863393
Topological Polar Surface Area:23.6
Heavy Atom Count:18
Complexity:356
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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