SENECIONINE

Bezeichnung:SENECIONINE

CAS-Nr130-01-8

Englisch Name:SENECIONINE

CBNumberCB6491042

SummenformelC18H25NO5

Molgewicht335.39

MOL-Datei130-01-8.mol

SENECIONINE physikalisch-chemischer Eigenschaften

Schmelzpunkt	236 °C(lit.)
alpha	D25 -55.1° (c = 0.034 in chloroform)
Siedepunkt	472.03°C (rough estimate)
Dichte	1.266 g/cm3
Brechungsindex	1.5100 (estimate)
storage temp.	−20°C
Löslichkeit	DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 0.1 mg/ml
Aggregatzustand	Solid
pka	12.81±0.40(Predicted)
Farbe	White to off-white
Optische Aktivität	[α]25/D 55.1°, c = 0.034% in chloroform
BRN	8162955
InChIKey	HKODIGSRFALUTA-JTLQZVBZSA-N
LogP	0.880 (est)
EPA chemische Informationen	Senecionine (130-01-8)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25
S-Sätze:	45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	VT5710000
F	10-23
HazardClass	6.1(a)
PackingGroup	II
Giftige Stoffe Daten	130-01-8(Hazardous Substances Data)
Toxizität	LD50 i.v. in mice: 64.12 ±2.24 mg/kg (Harris)

Gefahreninformationscode (GHS)

SENECIONINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
This hepatotoxic alkaloid is widely distributed among the Senecio species, being found in S. aureus, S. ilicifolius Thunb., S. integerrirnus, S. pseudaarnica, S. squaUdus, S. viscosus and S. vulgaris. The base is laevorotatory with [α]_D - 54.6° (CHCI₃ ) and the crystals sublime at 130-140°CfO.2 mm. The nitrate has m.p. 214°C;[α]_D - 34.2° (H₂ 0); the aurichloride, m.p. 186°C; the picrate, m.p. 191°C and the methiodide, m.p. 249°C. Alkaline hydrolysis furnishes retronecine and senecic acid (6-hydroxy-5-methyl-2-heptene-3 :6-dicarboxylic acid).
Beschreibung
Senecionine is a pyrrolizidine alkaloid that has been found in S. vulgaris and has hepatotoxic properties. It is metabolized by the cytochrome P450 (CYP) isoform CYP3A in the liver to the detoxification product senecionine N-oxide and reactive metabolites including dehydropyrrolizidine alkaloids and dehydrotetronecine. Senecionine (20 μM) induces mitochondrial depolarization and fragmentation in primary cultured mouse hepatocytes and increases apoptosis in a concentration-dependent manner. In rats, senecionine (35 mg/kg, p.o.) induces liver injury, increases serum levels of bilirubin and various bile acids, including taurocholic acid, glycocholic acid, and deoxycholic acid, and increases the activity of alanine aminotransferase and aspartate aminotransferase in serum. Senecionine-induced hepatotoxicity is associated with lipid peroxidation and glutathione depletion.
Verwenden
Senecionine is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells.
Definition
ChEBI: A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.
Sicherheitsprofil
Poison by intravenous,intraperitoneal, and possibly other routes. Anexperimental teratogen. Other experimental reproductiveeffects. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx.
Einzelnachweise
Grandval, Lajoux., Cornpt. rend., 120,1120 (1895)
Grandval, Lajoux., Bull. Soc. Chirn. Fr., 13,942 (1895)
Manske., Can. J. Res., S, 651 (1931)
Manske., ibid, 14B, 6 (1936)
Barger, Blackie., J. Chern. Soc., 584 (1937)
Blackie., Pharrn. J., 138,102 (1937)
Manske., Can. J. Res., 17B, I (1939)

SENECIONINE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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