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HomeProduct name listSENECIONINE

SENECIONINE

Synonym(s):Aureine

  • CAS NO.:130-01-8
  • Empirical Formula: C18H25NO5
  • Molecular Weight: 335.39
  • MDL number: MFCD00221720
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-08 21:13:59
SENECIONINE Structural

What is SENECIONINE?

Description

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.

Description

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).

The Uses of SENECIONINE

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.

Safety Profile

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.

References

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)

Properties of SENECIONINE

Melting point: 236 °C(lit.)
Boiling point: 472.03°C (rough estimate)
alpha  D25 -55.1° (c = 0.034 in chloroform)
Density  1.266 g/cm3
refractive index  1.5100 (estimate)
storage temp.  −20°C
solubility  DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 0.1 mg/ml
pka 12.81±0.40(Predicted)
form  Solid
form  neat
color  White to off-white
optical activity [α]25/D 55.1°, c = 0.034% in chloroform
BRN  8162955
EPA Substance Registry System Senecionine (130-01-8)

Safety information for SENECIONINE

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
Precautionary Statement Codes P262:Do not get in eyes, on skin, or on clothing.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for SENECIONINE

InChIKey HKODIGSRFALUTA-JTLQZVBZSA-N

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