SENECIONINE Property

Melting point:

236 °C(lit.)

alpha 

D25 -55.1° (c = 0.034 in chloroform)

Boiling point:

472.03°C (rough estimate)

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

color 

White to off-white

optical activity

[α]25/D 55.1°, c = 0.034% in chloroform

BRN 

8162955

InChIKey

HKODIGSRFALUTA-JTLQZVBZSA-N

LogP

0.880 (est)

EPA Substance Registry System

Senecionine (130-01-8)

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

VT5710000

F 

10-23

HazardClass 

6.1(a)

PackingGroup 

II

Hazardous Substances Data

130-01-8(Hazardous Substances Data)

Toxicity

LD50 i.v. in mice: 64.12 ±2.24 mg/kg (Harris)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

SENECIONINE Chemical Properties,Usage,Production

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).

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.

Uses

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)