(-)-sparteine
7,14-methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14abeta))-
 
Notes:
a quinolizidine alkaloid isolated from several fabaceae including lupinus; spartium; and cytisus. it has been used as an oxytocic and an anti-arrhythmia agent. it has also been of interest as an indicator of cyp2d6 genotype.
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      Product(s):
      S0461 (-)-Sparteine >98.0%(GC)
       
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CAS Number: 90-39-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 201-988-8
FDA UNII: 298897D62S
Nikkaji Web: J69.077E
MDL: MFCD00069653
XlogP3-AA: 2.50 (est)
Molecular Weight: 234.38622000
Formula: C15 H26 N2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 1.02000 @  25.00 °C.
Refractive Index: 1.52600 to 1.53000 @  20.00 °C.
Melting Point: 30.50 °C. @ 760.00 mm Hg
Boiling Point: 325.00 °C. @ 760.00 mm Hg
Flash Point: > 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): 3.210 (est)
Soluble in:
 water, 3040 mg/L @ 22 °C (exp)
 water, 1374 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
ExtraSynthese
For experimental / research use only.
Sparteine
Sigma-Aldrich: Aldrich
For experimental / research use only.
(-)-Sparteine 99%
TCI AMERICA
For experimental / research use only.
(-)-Sparteine >98.0%(GC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-dog LD50  15 mg/kg
Veterinary and Human Toxicology. Vol. 41, Pg. 33, 1999.

intramuscular-frog LDLo  1665 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1398, 1935.

intraperitoneal-guinea pig LDLo  23 mg/kg
Journal of Agricultural Research Vol. 32, Pg. 51, 1926.

intravenous-guinea pig LDLo  27 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: TREMOR
Planta Medica. Vol. 50, Pg. 420, 1984.

intraperitoneal-mouse LD50  36 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Planta Medica. Vol. 50, Pg. 420, 1984.

oral-mouse LD50  220 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: TREMOR
Planta Medica. Vol. 50, Pg. 420, 1984.

intravenous-rabbit LDLo  30 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1398, 1935.

intraperitoneal-rat LD50  42 mg/kg
Compilation of LD50 Values of New Drugs.

oral-rat LD50  960 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 210, Pg. 27, 1974.

Dermal Toxicity:
subcutaneous-frog LDLo 3330 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1398, 1935.

subcutaneous-mouse LD50 105 mg/kg
Pharmacology and Toxicology. English translation of FATOAO. Vol. 21, Pg. 468, 1958.

subcutaneous-rabbit LDLo 100 mg/kg
"Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 589, 1948.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for (-)-sparteine usage levels up to:
 not for fragrance use.
 
Recommendation for (-)-sparteine flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 7014
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
Chemidplus: 0000090391
RTECS: WG5950000 for cas# 90-39-1
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References:
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 7014
Pubchem (sid): 134970944
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2921.30.3000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 esparteina
 genisteine alkaloid
 lupinidine
7,14-methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-
7,14-methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14abeta))-
6-beta,7-alpha,9-alpha,11-alpha-pachycarpine
 sparteina
L-sparteine
 sparteinum
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Articles:
PubMed: Evaluation of total quinolizidine alkaloids content in lupin flours, lupin-based ingredients, and foods.
PubMed: Bacterial removal of quinolizidine alkaloids and other carbon sources from a Lupinus albus aqueous extract.
PubMed: Chemical composition, nutritive value, and toxicology evaluation of Mexican wild lupins.
PubMed: A novel generation of coupling reagents. Enantiodifferentiating coupling reagents prepared in situ from 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and chiral tertiary amines.
PubMed: Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture.
PubMed: A 90-day feeding study of the alkaloids of Lupinus angustifolius in the rat.
PubMed: A new bioassay for testing plant extracts and pure compounds using red flour beetleTribolium castaneum Herbst.
PubMed: Potentially hazardous compound in a herbal slimming remedy.
PubMed: Effects of dietary protein and lupine alkaloids on growth and survivorship ofSpodoptera eridania.
PubMed: Reinvestigation of the alkaloids of Lupinus sericeus Pursh. Identification of a new natural product, 10,17-dioxo-beta-isosparteine.
PubMed: [Lupins - a new source of food for Andean countries. 5. Traditional methods of debittering of lupins by water].
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