DC Chemicals Limited
China
Product Name: Retrorsine
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Purity: 98.0%
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480-54-6

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: 2024-01-14 19:08:07
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	Research Areas >> Others Signaling Pathways >> Others >> Others
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
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
69102-07-4
DownStream 1
74164-84-4