U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H26N2
Molecular Weight 234.3809
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-ISOSPARTEINE

SMILES

C1CCN2C[C@]3([H])C[C@@]([H])(CN4CCCC[C@]34[H])[C@@]2([H])C1

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

HIDE SMILES / InChI

Molecular Formula C15H26N2
Molecular Weight 234.3809
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Originator

Curator's Comment:: a-Isosparteine was first unequivocally obtained by Winterfeld K. and Rauch C. in 1934 DOI: 10.1002/ardp.19342721013

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The papilionaceous alkaloids. XI. Identity of genisteine with 1-alpha-isosparteine.
1951 Apr
Alkaloids from Lupinus argenteus var. stenophyllus.
1978 Mar
(-)-alpha-Isosparteine from Lupinus argenteus var. stenophyllus.
1983 May
New mammalian metabolites of sparteine.
1990
Total synthesis of (+/-)-alpha-isosparteine, (+/-)-beta-isosparteine, and (+/-)-sparteine from a common tetraoxobispidine intermediate.
2008 Oct 17
Patents

Patents

Sample Use Guides

Rat: 50 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:19:25 UTC 2021
Edited
by admin
on Sat Jun 26 03:19:25 UTC 2021
Record UNII
94BIS8AH96
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-ISOSPARTEINE
Common Name English
ISOSPARTEINE, ALPHA-
Common Name English
(7S-(7.ALPHA.,7A.ALPHA.,14.ALPHA.,14A.ALPHA.))-DODECAHYDRO-7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE
Common Name English
.ALPHA.-ISOSPARTEIN
Common Name English
(-)-.ALPHA.-ISOSPARTEINE
Common Name English
.ALPHA.-ISOSPARTEINE, (-)-
Common Name English
.ALPHA.-SPARTEINE
Common Name English
11-ISOSPARTEINE
Common Name English
SPARTEINE L-.ALPHA.-ISOSPARTEINE
MI  
Common Name English
GENISTEINE
Common Name English
GENISTEINE-ALKALOID
Common Name English
SPARTEINE L-.ALPHA.-ISOSPARTEINE [MI]
Common Name English
NSC-366737
Code English
7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE, DODECAHYDRO-, (7S,7AR,14S,14AR)-
Common Name English
7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE, DODECAHYDRO-, (7S-(7.ALPHA.,7A.ALPHA.,14.ALPHA.,14A.ALPHA.))-
Common Name English
Code System Code Type Description
CAS
446-95-7
Created by admin on Sat Jun 26 03:19:25 UTC 2021 , Edited by admin on Sat Jun 26 03:19:25 UTC 2021
PRIMARY
PUBCHEM
92759
Created by admin on Sat Jun 26 03:19:25 UTC 2021 , Edited by admin on Sat Jun 26 03:19:25 UTC 2021
PRIMARY
MERCK INDEX
M10134
Created by admin on Sat Jun 26 03:19:25 UTC 2021 , Edited by admin on Sat Jun 26 03:19:25 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
207-177-5
Created by admin on Sat Jun 26 03:19:25 UTC 2021 , Edited by admin on Sat Jun 26 03:19:25 UTC 2021
PRIMARY
FDA UNII
94BIS8AH96
Created by admin on Sat Jun 26 03:19:25 UTC 2021 , Edited by admin on Sat Jun 26 03:19:25 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT