RETRORSINE
RETRORSINE Basic information
- Product Name:
- RETRORSINE
- Synonyms:
-
- BETA-LONGILOBINE
- 12,18-DIHYDROXYSENECIONAN-11,16-DIONE
- RETRORSIN
- RETRORSINE
- 16-dione,12,18-dihydroxy-senecionan-1
- 5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-hydroxymethyl-5-3-ethylidene-4
- cis-retronecicacidesterofretronecine
- methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione
- CAS:
- 480-54-6
- MF:
- C18H25NO6
- MW:
- 351.39
- EINECS:
- 610-403-9
- Mol File:
- 480-54-6.mol
RETRORSINE Chemical Properties
- Melting point:
- 208-211 °C (lit.)
- alpha
- D18 -17.6° (c = 1.99 in ethanol)
- Boiling point:
- 485.2°C (rough estimate)
- Density
- 1.32±0.1 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.5100 (estimate)
- storage temp.
- 2-8°C
- pka
- 12.00±0.40(Predicted)
- form
- Solid
- color
- White to off-white
- Merck
- 13,8253
- InChIKey
- BCJMNZRQJAVDLD-VMOBWIEOSA-N
- CAS DataBase Reference
- 480-54-6
- IARC
- 3 (Vol. 10, Sup 7) 1987
- EPA Substance Registry System
- Retrorsine (480-54-6)
Safety Information
- Hazard Codes
- T
- Risk Statements
- 25
- Safety Statements
- 22-36/37/39-45
- RIDADR
- 1544
- WGK Germany
- 3
- RTECS
- VH7525000
- HazardClass
- 6.1(a)
- PackingGroup
- II
- Hazardous Substances Data
- 480-54-6(Hazardous Substances Data)
RETRORSINE Usage And Synthesis
Uses
Retrorsine-D4 is a labelled analogue of Retrorsine (R279000). Retrorsine is a pyrrolizidine alkaloid that blocks the hepatocyte cell cycle, ultimately affecting hepatocyte proliferative capacity.
Definition
ChEBI: Retrorsine is a macrolide.
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Safety Profile
Poison by ingestion, intraperitoneal, and intravenous routes. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. hhtation data reported. When heated to decomposition it emits toxic fumes of NOx.
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[4].
| Animal Model: | Male Wistar rats (180±20 g), portal branch ligation (PBL) model[4] |
| 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. |
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RETRORSINE(480-54-6)Related Product Information
- ALLYL ISOVALERATE
- 3-METHOXYPYRROLIDINE
- (2-Propenyloxy)propanol
- Butyl hydroxyacetate
- 3-ALLYLOXY-1,2-PROPANEDIOL
- 2-Dimethylaminoethyl acetate
- DIMETHYL 2-METHYLADIPATE
- 3-Butoxypropanamine
- 2-HYDROXY-3-METHYLBUTYRIC ACID
- 3-Pyrrolidinol
- 2-HYDROXY-N-BUTYRIC ACID ETHYL ESTER
- RETRORSINE
- Methyl (R)-(+)-lactate
- ISO-PROPYL ACRYLATE
- ISOBUTYRIC ACID N-PROPYL ESTER
- 3-(DIMETHYLAMINO)PROPYL ACRYLATE
- 1-AMINO-5-HEXENE
- 2-METHYL-5-HEXEN-2-OL