U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of .ALPHA.-ISOSPARTEINE

SMILES

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

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 234.3803
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
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 Mon Mar 31 20:06:17 GMT 2025
Edited
by admin
on Mon Mar 31 20:06:17 GMT 2025
Record UNII
94BIS8AH96
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SPARTEINE L-.ALPHA.-ISOSPARTEINE
MI  
Preferred Name English
.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
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 Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
CHEBI
81074
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
PUBCHEM
92759
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
MERCK INDEX
m10134
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
207-177-5
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
NSC
366737
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID601126235
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
FDA UNII
94BIS8AH96
Created by admin on Mon Mar 31 20:06:17 GMT 2025 , Edited by admin on Mon Mar 31 20:06:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT