fulvine
fulvine Basic information
- Product Name:
- fulvine
- Synonyms:
-
- fulvine
- 13-Epicrispatine
- 20-Norcrotalanan-11,15-dione, 14,19-dihydro-13-hydroxy-, (12-xi,13-xi)-
- Brn 1088365
- Fulvine (8ci)
- Nsc 89932
- 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4-hydroxy-3,4,5-trimethyl-, (3R,4S,5S,13aR,13bR)- (9CI)
- CAS:
- 6029-87-4
- MF:
- C16H23NO5
- MW:
- 309.36
- Mol File:
- 6029-87-4.mol
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fulvine Chemical Properties
- Melting point:
- 212.5°C
- Boiling point:
- 449.63°C (rough estimate)
- Density
- 1.1188 (rough estimate)
- refractive index
- 1.5500 (estimate)
- pka
- 13.53±0.60(Predicted)
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fulvine Usage And Synthesis
Uses
Fulvine is a pyrrolizidine alkaloid isolated from the seeds of Crotalaria fulva. Fulvine is hepatotoxic and can be used to induce hypertensive pulmonary vascular disease in vivo[1].
Definition
ChEBI: Fulvine is a member of pyrrolizines.
Safety Profile
Poison by intraperitoneal route. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
in vivo
Fulvine can be used in animal modeling to create respiratory disease models[1][2].
Induction of respiratory and liver disease[1][2].
Background
Fulvine on reaching the liver is metabolically converted into a cellular toxin. Some of this toxin is retained in the hepatic cells, and produces
necrosis and other cellular changes. Some of the toxin escapes to damage the vascular endothelium in the hepatic veins. This may take the form of endothelial proliferation with the later changes characteristic of veno-occlusion. Carried further, the escaping toxic metabolites reach the pulmonary tissues to produce vascular changes with increased capillary permeability and progressive oedema and cellular changes in the lungs, including the development of the big cells and the accumulation of mast cells[2].
Specific Modeling Methods
Rat: White SPF and conventional? Male and Female? weighing 50-65 g and 45-60 g[1]
Administration: 30-45 mg/kg? neutralised aqueous solution by stomach tube? a single dose[1]
Rat: Male and Female? weighing 40-80 g[2]
Administration: 50 mg/kg? given by stomach tube? a single dose[2]
Administration: 30-45 mg/kg? neutralised aqueous solution by stomach tube? a single dose[1]
Rat: Male and Female? weighing 40-80 g[2]
Administration: 50 mg/kg? given by stomach tube? a single dose[2]
Note
(1)SPF rats and conventional rats were kept separately. All were weighed at least weekly. Rats that died or were killed with coal-gas when ill were examined post mortem. Lungs, liver and other tissues from representative animals were fixed in Hefly’s fluid; paraffin sections were stained with haematoxylin and eosin[1]
.
Crystalline Fulvine was dissolved in dilute hydrochloric acid, neutralised and diluted to give a 1% solution[2]
.
.
Crystalline Fulvine was dissolved in dilute hydrochloric acid, neutralised and diluted to give a 1% solution[2]
.
Modeling Indicators
Pathology change: The lungs were congested or oedematous and did not collapse when the chest was opened, showing petechiae or small dark red patches. Large often bloodstained, effusions were present in many rats. The liver appeared enlarged, dark red with a brownish tint, slightly granular and rubbery. The heart seemed enlarged; some rats had gastro-intestinal haemorrhage and prominent red lymph-glands. Varying degrees of ascites were present, and the ventral skin was often oedematous[1]
.
Behavioral observation: Fulvine induced some developed difficulty in breathing and slowing or cessation of growth in rats[1]
.
Histological analysis: Fulvine induced moderate ascites, well marked fibrous thickening of the central vein walls, endothelial proliferation and some perivascular centrilobular fibrosis with possibly partial venous occlusion[2]
.
.
Behavioral observation: Fulvine induced some developed difficulty in breathing and slowing or cessation of growth in rats[1]
.
Histological analysis: Fulvine induced moderate ascites, well marked fibrous thickening of the central vein walls, endothelial proliferation and some perivascular centrilobular fibrosis with possibly partial venous occlusion[2]
.
Correlated Product(s): Monocrotaline (HY-N0750); Crispatine
Opposite Product(s): /
References
[1] Schoental R. Rat lung lesions due to Fulvine. J Pathol Bacteriol. 1966 Apr;91(2):629-31. DOI:10.1002/path.1700910246
[2] BARNES JM, et al. LESIONS IN THE LUNGS AND LIVERS OF RATS POISONED WITH THE PYRROLIZIDINE ALKALOID Fulvine AND ITS N-OXIDE. J Pathol Bacteriol. 1964 Oct;88:521-31. DOI:10.1002/path.1700880215
[3] J M Kay, et al.Fulvine and the pulmonary circulation. Thorax DOI:10.1136/thx.26.3.249
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