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Related CAS#:
130-01-8 641-12-3
13268-67-2 28379-63-7
126642-77-1

130-01-8

130-01-8 structure
130-01-8 structure
  • Name: Senecionine
  • Chemical Name: senecionine
  • CAS Number: 130-01-8
  • Molecular Formula: C18H25NO5
  • Molecular Weight: 335.395
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-03-06 08:00:00
  • Modify Date: 2024-01-13 15:31:23
  • Senecionine is a pyrrolizidine alkaloid isolated from Senecio vulgaris. Senecionine is toxic to animals and humans.
Name senecionine
Synonyms (3Z,5R,6R,14aR,14bR)-3-éthylidène-6-hydroxy-5,6-diméthyl-3,4,5,6,9,11,13,14,14a,14b-décahydro[1,6]dioxacyclododécino[2,3,4-gh]pyrrolizine-2,7-dione
aureine
Senecionine
MFCD00221720
(3Z,5R,6R,14aR,14bR)-3-Ethyliden-6-hydroxy-5,6-dimethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-2,7-dion
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
(3Z,5R,6R,14aR,14bR)-3-Ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
(15Z)-12-Hydroxysenecionan-11,16-dione
Integerrimine
Description Senecionine is a pyrrolizidine alkaloid isolated from Senecio vulgaris. Senecionine is toxic to animals and humans.
Related Catalog
In Vitro Pyrrolizidine alkaloids (PAs) are considered to be one of the most hepatotoxic groups of compounds of plant origin and are present in about 3% of the world's flowering plants. Most PAs represent a considerable health hazard to both livestock and humans through the consumption of plants and PA-contaminated products such as milk, honey, herbal teas, and medicines[1].
In Vivo Upon intravenous administration and oral administration of Senecionine and Adonifoline, significant differences in pharmacokinetics were observed, with the Senecionine and Adonifoline being absorbed fast with lower bioavailability and being quickly metabolized to PA N-oxides and hydroxylation products of PAs or their N-oxides[1]. Senecionine fails to stimulate epoxide hydrase, it diminishs the activity of glutathione-s-transferase, aminopyrine demethylase and AHH[2]. Twice-weekly injections of a third constituent, senecionine, beginning on Day 12 or later, results in premature deliveries in three of seven rats, and the pups from all litters are stillborn or die shortly after birth[3].
Animal Admin Rats[1] Swiss albino rats weighing 155-175 g are incubated for 3 consecutive days with seneciphylline and senecionine at a daily dose of 40 or 80 mg/kg body wt. Control animals received normal saline only. The animals are killed 24 h after the last dose. The livers are removed, weighed and then homogenized in 1.15% KCI, 0.02 HEPES (pH 7.4)[1].
References

[1]. Wang C, et al. The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Anal Bioanal Chem. 2011 Jul;401(1):275-87.

[2]. Kakrani HK, et al. Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats. J Ethnopharmacol. 1984 Dec;12(3):271-8.

[3]. Tu ZB, et al. Identification of senecionine and senecionine N-oxide as antifertility constituents in Senecio vulgaris. J Pharm Sci. 1988 May;77(5):461-3.
Density 1.3±0.1 g/cm3
Boiling Point 563.7±50.0 °C at 760 mmHg
Melting Point 236ºC(lit.)
Molecular Formula C18H25NO5
Molecular Weight 335.395
Flash Point 294.7±30.1 °C
Exact Mass 335.173279
PSA 76.07000
LogP 0.88
Vapour Pressure 0.0±3.5 mmHg at 25°C
Index of Refraction 1.570

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VT5710000
CHEMICAL NAME :
Senecionan-11,16-dione, 12-hydroxy-
CAS REGISTRY NUMBER :
130-01-8
LAST UPDATED :
199612
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C18-H25-N-O5
MOLECULAR WEIGHT :
335.44
WISWESSER LINE NOTATION :
T55-12- 1A Q EN IOVY OVO BUTJ KU2 M NQ N

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
85 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
33 mg/kg
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
41200 ug/kg
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
64 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
61 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - acute pulmonary edema Liver - hepatitis (hepatocellular necrosis), diffuse Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
140 mg/kg
SEX/DURATION :
female 4-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
Sex chromosome loss and nondisjunction

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
90 mg/kg
REFERENCE :
TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 1,42,1981 *** REVIEWS *** TOXICOLOGY REVIEW ZKKOBW Zeitschrift fuer Krebsforschung und Klinische Onkologie. (Berlin, Fed. Rep. Ger.) V.76-92, 1971-78. For publisher information, see JCROD7. Volume(issue)/page/year: 78,99,1972
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Hazard Codes T
Risk Phrases R25
Safety Phrases 45
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS VT5710000
Packaging Group II
Hazard Class 6.1(a)
Precursor  0

DownStream  1


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