CAS 130-01-8|Senecionine

Introduction：Basic information about CAS 130-01-8|Senecionine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Senecionine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles26
7. Synonyms

Common Name	Senecionine
CAS Number	130-01-8	Molecular Weight	335.395
Density	1.3±0.1 g/cm3	Boiling Point	563.7±50.0 °C at 760 mmHg
Molecular Formula	C₁₈H₂₅NO₅	Melting Point	236ºC(lit.)
MSDS	ChineseUSA	Flash Point	294.7±30.1 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	senecionine
Synonym	More Synonyms

Senecionine BiologicalActivity

Description	Senecionine is a pyrrolizidine alkaloid isolated from Senecio vulgaris. Senecionine is toxic to animals and humans.
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Metabolic Disease
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.

Chemical & Physical Properties

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
InChIKey	HKODIGSRFALUTA-JTLQZVBZSA-N
SMILES	CC=C1CC(C)C(C)(O)C(=O)OCC2=CCN3CCC(OC1=O)C23

Toxicological Information

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

Safety Information

Symbol	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)

Articles26

UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed.

Food Chem. 170 , 265-70, (2014)

Alkaloids known as secondary metabolites are grouped by typical structural characteristics into large families such as pyrrolizidine alkaloids (PAs) comprising more than 350 individual heterocyclic co...

Modeling K(m) values using electrotopological state: substrates for cytochrome P450 3A4-mediated metabolism.

Bioorg. Med. Chem. Lett. 15 , 4076-84, (2005)

In order to determine K(m) values of substrates for CYP3A4-mediated metabolism, an in silico model has been developed in the present work. Using electrotopological state (E-state) indices, together wi...

A competitive enzyme immunoassay for the pyrrolizidine alkaloids of the senecionine type.

Planta Med. 62(3) , 267-71, (1996)

We developed an immunoassay with antibodies against retrorsine to detect the closely related senecionine, the main alkaloid in various Asteraceae. Sensitivity is about 23 pg (68 fmol) for 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

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