Basic information
- CAS
90-39-1- Standard SMILES
C1CCN2C[C@@H]3C[C@@H](CN4CCCC[C@@H]34)[C@H]2C1- InChIKey
SLRCCWJSBJZJBV-ZQDZILKHSA-N- Molecular formula
- C15H26N2
- Average molar mass
- 234.38 g/mol
- Monoisotopic mass
- 234.20959883
Overview
Sparteine is a quinolizidine alkaloid and a quinolizidine alkaloid fundamental parent.
Names & identifiers
- Preferred name
- Sparteine
- IUPAC
- (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
- English name
- (-)-SPARTEINE
- Molecular formula
- C15H26N2
- Molecular weight
- 234.38
Names & synonyms
(-)-SparteineSparteine90-39-1L-SPARTEINEEsparteinaLupinidinSparteinaSparteinumGenisteine AlkaloidDTXSID40235916beta,7alpha,9alpha,11alpha-Pachycarpine6-beta,7-alpha,9-alpha,11-alpha-Pachycarpine
Show more names
(?)-SparteineSpartineLUPINIDINESparteineulexineLupinindin1-Sparteine(-)-spartein
DTXCID403591298897D62SCHEBI:28827alpha Isosparteine(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14abeta))-7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, [7S-(7alpha,7aalpha,14alpha,14abeta)]-beta Isosparteine
Database identifiers
- CAS
90-39-1- PubChem CID
- 644020
- DTXSID
DTXSID4023591- ChEMBL
CHEMBL1908847- ChEBI
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 6.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 263
Experimental & physicochemical properties
SpringerMaterials PropertiesCrystal structure
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section152.34 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 30.5 °C · 30.5°C
- Boiling point
- 137 · 137-138 °C1 mm Hg(lit.)
- alpha
- 21 · D21 -16.4° (c = 10 in abs alc)
- Density
- 1.02 g/mL · 1.02 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.528(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethanol (Slightly)
- form
- liquid
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- WG5950000
- ridadr
- 3140
- hs_code
- 2933399990
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- hazard_class
- 6.1(b)
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- Hazard statements
- H302+H312+H332
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Metabolism/MetabolitesSparteine has known human metabolites that include Sparteine, 13-hydroxy, 14-Hydroxysparteine, and Retamine.
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157)
Uses & manufacturing
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
DescriptionSparteine is effective against sinoatrial and atrial tachycardias, atrial extrasystoles, and also against ventricular arrhythmias . Despite prolongation of the myocardial refractory period in vitro, theECGtimes are not prolonged in vivo.
UsesSparteine occurs in yellow and black lupinbeans (Lupinus luteus L. and L. niger). Italso occurs in other Lupinus species aswell as in Cytisus and Spartium species.Therapeutically, it is used as an oxytocicagent.
Related reactions
31 records
Compound notes
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