Description
Seneciphylline, a natural pyrrolizidine alkaloid isolated from the herbs of Senecio scandens, may cause reduction of cytochrome P-450 and related monooxygenase activities. Seneciphylline is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells. In vitro, seneciphylline has no effection on hepatic drug metabolizing enzymes, but has seneciphyllineslight activity of reducing aminopyrine demethylase.
Synonyms
Jacodine; (15cis)-12-Hydroxy-13,19-didehydrosenecionan-11,16-dione; 13,19-didehydro-12-hydroxysenecionan-11,16-dione
IUPAC Name
(1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
Molecular Formula
C18H23NO5
Canonical SMILES
CC=C1CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O
InChI
InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/m1/s1
InChIKey
FCEVNJIUIMLVML-QPSVUOIXSA-N
Boiling Point
470.34°C (rough estimate)
Solubility
less than 0.1 mg/mL at 64 °F
Alpha
D -128° (chloroform)
pKa
12.43±0.20(Predicted)
Refractive Index
1.5740 (estimate)
Risk Statements
23/24/25-25
Safety Statements
1-20-24/25-45
Stability
Stable, but reacts with oxygen in the air. Incompatible with alkali, oxidizing agents. Store under inert gas.
Uses
Seneciphylline is a minor constituent of S. jacobaea, which has been used as a medicinal herb. It has the effect of coagulation and hemostasis.Seneciphylline is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells.