isatidine

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Names

[ CAS No. ]:
480-54-6

[ Name ]:
isatidine

[Synonym ]:
(15Z)-12,18-Dihydroxysenecionan-11,16-dione
[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-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-
isatidine
trans-15-Ethylidene-12b-hydroxy-12a-hydroxymethyl-13b-methylsenec-1-enine
b-Longilobine
12,18-dihydroxy-senecionane-11,16-dione
12,18-Dihydroxysenecionan-11,16-dione
β-Longilobine
cis-Retronecic acid ester of retronecine
Retrorsin
(3Z,5R,6S,14aR,14bR)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
MFCD00013331

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
583.2±50.0 °C at 760 mmHg

[ Melting Point ]:
208-211ºC(lit.)

[ Molecular Formula ]:
C₁₈H₂₅NO₆

[ Molecular Weight ]:
351.394

[ Flash Point ]:
306.5±30.1 °C

[ Exact Mass ]:
351.168182

[ PSA ]:
96.30000

[ LogP ]:
-0.14

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.590

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VH7525000

CHEMICAL NAME :: Retrorsine

CAS REGISTRY NUMBER :: 480-54-6

LAST UPDATED :: 199512

DATA ITEMS CITED :: 22

MOLECULAR FORMULA :: C18-H25-N-O6

MOLECULAR WEIGHT :: 351.44

WISWESSER LINE NOTATION :: T55-12- 1A Q EN IOVY OVO BUTJ KU2 M1 NQ N1Q

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 :: 34 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 38 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 :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 35 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 65 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 :: 59 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 :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 46 mg/kg

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Liver - other changes Blood - macrocytosis

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 33 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 175 mg/kg/5D-I

TOXIC EFFECTS :: Liver - other changes Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 560 mg/kg/62W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 150 mg/kg/22W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68 mg/kg/43W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Kidney, Ureter, Bladder - Kidney tumors

TYPE OF TEST :: Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 3160 nmol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 282,169,1992 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,303,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,303,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
25

[ Safety Phrases ]:
S22;S45;S36/S37/S39

[ RIDADR ]:
UN 1544

[ RTECS ]:
VH7525000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Precursor & DownStream

Precursor

DownStream

Articles

Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): implications for toxicity.

Phytochemistry 108 , 137-46, (2014)

Changes in plant chemical defenses after invasion could have consequences on the invaded ecosystems by modifying the interactions between plants and herbivores and facilitating invasion success. Howev...

Involvement of organic cation transporter 1 and CYP3A4 in retrorsine-induced toxicity.

Toxicology 322 , 34-42, (2014)

Retrorsine (RTS) is a hepatotoxic pyrrolizidine alkaloid present in plants of the Senecio genus. The present study is aimed at clarifying the role of organic cation transporters (OCTs) in the liver di...

Are effects of common ragwort in the Ames test caused by pyrrolizidine alkaloids?

Mutat. Res. 778 , 1-10, (2015)

It has previously been demonstrated by others that acetone extracts of Senecio jacobaea (syn. Jacobaea vulgaris, common or tansy ragwort) test positive in the Salmonella/microsome mutagenicity test (A...