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480-54-6

480-54-6 structure
480-54-6 structure
  • Name: isatidine
  • Chemical Name: retrorsine
  • CAS Number: 480-54-6
  • Molecular Formula: C18H25NO6
  • Molecular Weight: 351.394
  • Catalog: analytical chemistry Standard Food and cosmetics standards
  • Create Date: 2018-09-05 06:07:01
  • Modify Date: 2025-08-20 19:36:36
  • Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes[1][2].
Name retrorsine
Synonyms (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
Description Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes[1][2].
Related Catalog
In Vitro Retrorsine (60-240 μM; 24 hours) significantly reduces HSEC-CYP3A4 cells viability, depletes GSH, and increases formation of pyrrole-protein adducts[3]. Cell Viability Assay[3] Cell Line: HSEC-CYP3A4 cells Concentration: 60 μM, 120 μM , 240 μM Incubation Time: 24 hours Result: Significantly decreased cell viability.
In Vivo Retrorsine (30 mg/kg; i.p.; twice) impairs liver regeneration in the PBL model not only by an S or G2/M phase block, but also by a block located before the G1/S transition of the cell cycle[1]. Animal Model: Male Wistar rats (180±20 g), portal branch ligation (PBL) model[1] Dosage: 30 mg/kg Administration: Intraperitoneal injection, twice, separated by 2-week interval Result: Strongly impaired the liver weight gain, protein and DNA synthesis as well as induction of cell cycle related proteins in the regenerating lobes after PBL.
References

[1]. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46.

[2]. F J Cubero, et al. Hepatic proliferation in Gunn rats transplanted with hepatocytes: effect of retrorsine and tri-iodothyronine. Cell Prolif. 2005 Jun;38(3):137-46.

[3]. Yao Lu, et al. Establishment of a novel CYP3A4-transduced human hepatic sinusoidal endothelial cell model and its application in screening hepatotoxicity of pyrrolizidine alkaloids. J Environ Sci Health C Toxicol Carcinog. 2020;38(2):169-185.
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

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
Symbol GHS06
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  1

DownStream  1

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