Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H26N2 |
Molecular Weight | 234.3803 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CN3CCCC[C@]3([H])[C@]([H])(CN4CCCC[C@]14[H])C2
InChI
InChIKey=SLRCCWJSBJZJBV-BYNSBNAKSA-N
InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14+,15+/m0/s1
a-Isosparteine was originally isolated from Cytisus scoparius. It was isolated from two other legumes, Lupinus caudatus Kell. and Genista tinctoria L. a-Isosparteine exhibits basically the same action as does (-)-sparteine but possesses a more rapid onset and a shorter duration when compared using rat myocardial tissue. male Sprague-Dawley rats were found to metabolize sparteine and a-isosparteine to lupanine and alpha-isolupanine respectively in vivo. a-Isosparteine elicits intense interest because of its deployment as uniquely effective chiral ligand in a wide variety of metal-mediated enantioselective synthetic methods.
Approval Year
PubMed
Title | Date | PubMed |
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The papilionaceous alkaloids. XI. Identity of genisteine with 1-alpha-isosparteine. | 1951 Apr |
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Alkaloids from Lupinus argenteus var. stenophyllus. | 1978 Mar |
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(-)-alpha-Isosparteine from Lupinus argenteus var. stenophyllus. | 1983 May |
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New mammalian metabolites of sparteine. | 1990 |
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Total synthesis of (+/-)-alpha-isosparteine, (+/-)-beta-isosparteine, and (+/-)-sparteine from a common tetraoxobispidine intermediate. | 2008 Oct 17 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2388532
Rat: 50 mg/kg
Route of Administration:
Intraperitoneal
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446-95-7
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SUBSTANCE RECORD