Sparteine (HCID 644020)

Überblick

Sparteine is a quinolizidine alkaloid and a quinolizidine alkaloid fundamental parent.

Namen und Bezeichner

Bevorzugter Name: Sparteine
IUPAC: (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
Lokaler Name: Spartein
Englischer Name: (-)-SPARTEINE
Summenformel: C15H26N2
Molmasse: 234.38

Namen und Synonyme

(-)-SparteineSparteine90-39-1L-SPARTEINEEsparteinaLupinidinSparteinaSparteinumGenisteine AlkaloidDTXSID40235916beta,7alpha,9alpha,11alpha-Pachycarpine6-beta,7-alpha,9-alpha,11-alpha-Pachycarpine

Weitere Namen anzeigen

(?)-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

Datenbank-Bezeichner

CAS: 90-39-1
PubChem CID: 644020
DTXSID: DTXSID4023591
ChEMBL: CHEMBL1908847
ChEBI: CHEBI:28827
UNII: 298897D62S
EC Number: 201-988-8
Nikkaji: J4.317F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,5
Polarare Oberfläche (TPSA): 6,5 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 0
Schwere Atome: 17
Formalladung: 0
Komplexität: 263

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesCrystal structure

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Collision Cross Section152.34 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 30.5 °C · 30.5°C
Siedepunkt: 137 · 137-138 °C1 mm Hg(lit.)
Dichte: 1.02 g/mL · 1.02 g/mL at 25 °C(lit.)
Brechungsindex: 20 · n20/D 1.528(lit.)
Flammpunkt: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
Löslichkeit: Chloroform (Slightly), Ethanol (Slightly)
Aggregatzustand: liquid
pka: 2.24 · 2.24, 9.46(at 20℃)
Farbe: Light Yellow to Yellow
Wasserlöslichkeit: 3.04 g/L · 3.04g/L(25 ºC)
Merck: 14 · 14,8737
BRN: 82447 · 82447
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
InChIKey: SLRCCWJSBJZJBV-ZQDZILKHSA-N
SMILES: C1CCN2C[C@@H]3C[C@@H](CN4CCCC[C@H]34)[C@@H]2C1
LogP: 3.21 · 3.210 (est)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory InformationRegulation (EC) No 178/2002 (amended)

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: 3
ridadr: 3140
hs_code: 2933399990
RTECS-Nr.: WG5950000
risk_code: 20/21/22
hazard_code: Xn
safety_code: 36
hazard_class: 6.1(b)
packing_group: III
Speicherklasse: 10 - Combustible liquids
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

C - Cardiovascular system

QC - Cardiovascular system

Metabolism/MetabolitesSparteine has known human metabolites that include Sparteine, 13-hydroxy, 14-Hydroxysparteine, and Retamine.

MeSH Pharmacological Classification · 2 Einträge

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)

Verwendung und Herstellung

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Anwendungen

VerwendenSparteine 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.