monocrotaline
(13-alpha,14-alpha)-14,19-dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
Identification
| Name | monocrotaline |
| CAS Number | 315-22-0 |
| FDA UNII | 73077K8HYV |
| Molecular Formula | C16 H23 N O6 |
| Molecular Weight | 325.36151000 |
| MDL Number | MFCD00084656 |
| Nikkaji Number | J107.104A |
| Beilstein | 0048732 |
Regulatory
Physical Properties
| Appearance | colorless prisms (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 537.30 °C. @ 760.00 mm Hg (est) |
| Flash Point | 534.00 °F. TCC ( 278.70 °C. ) (est) |
| logP (o/w) | -0.370 (est) |
| Soluble in | water, 9.019e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | unreported-mammal (species unspecified) LDLo 60 mg/kg |
| Dermal Toxicity | subcutaneous-rat LD50 60 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for monocrotaline usage levels up to | not for fragrance use. |
| Recommendation for monocrotaline flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
mono
crotalin
(13-alpha,14-alpha)-14,19-
dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
12-beta,13-beta-
dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine
20-
norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
(2,3,4-gh)
pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
PubMed:
UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed.
PubMed:
[Determination of five pyrrolizidine alkaloids in honey by liquid chromatography-tandem mass spectrometry].
PubMed:
Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed.
PubMed:
Diaphragm atrophy and contractile dysfunction in a murine model of pulmonary hypertension.
PubMed:
Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates.
PubMed:
Dehydropyrrolizidine alkaloids, including monoesters with an unusual esterifying acid, from cultivated Crotalaria juncea (Sunn Hemp cv.'Tropic Sun').
PubMed:
¹H NMR study of monocrotaline and its metabolites in human blood.
PubMed:
Anti-TNF treatment reduces rat skeletal muscle wasting in monocrotaline-induced cardiac cachexia.
PubMed:
Involvement of RhoA/Rho kinase signaling in protection against monocrotaline-induced pulmonary hypertension in pneumonectomized rats by dehydroepiandrosterone.
PubMed:
Anticoagulation and inhibition of nitric oxide synthase influence hepatic hypoxia after monocrotaline exposure.
PubMed:
Bosentan, sildenafil, and their combination in the monocrotaline model of pulmonary hypertension in rats.
PubMed:
Acquired and partially de novo synthesized pyrrolizidine alkaloids in two polyphagous arctiids and the alkaloid profiles of their larval food-plants.
PubMed:
Modes of cell death in rat liver after monocrotaline exposure.
PubMed:
The coagulation system contributes to synergistic liver injury from exposure to monocrotaline and bacterial lipopolysaccharide.
PubMed:
Endothelial cell injury and coagulation system activation during synergistic hepatotoxicity from monocrotaline and bacterial lipopolysaccharide coexposure.
PubMed:
Role of neutrophils in the synergistic liver injury from monocrotaline and bacterial lipopolysaccharide exposure.
PubMed:
The role of Kupffer cells and TNF-alpha in monocrotaline and bacterial lipopolysaccharide-induced liver injury.
PubMed:
The temporal relationship between bacterial lipopolysaccharide and monocrotaline exposures influences toxicity: shift in response from hepatotoxicity to nitric oxide-dependent lethality.
PubMed:
Temporal modulation of pyrrolizidine alkaloid intake and genetic variation in performance of Utetheisa ornatrix caterpillars.
PubMed:
Lack of protective action of cysteine against the fetotoxic effect of monocrotaline.
PubMed:
Synergistic hepatotoxicity from coexposure to bacterial endotoxin and the pyrrolizidine alkaloid monocrotaline.
PubMed:
Fetotoxicity and reproductive effects of monocrotaline in pregnant rats.
PubMed:
Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices.
PubMed:
Sexually transmitted chemical defense in a moth (Utetheisa ornatrix).
PubMed:
Metabolic activation of pyrrolizidine alkaloids by human, rat and avocado microsomes.
PubMed:
Dietary restriction, polyamines and monocrotaline-induced pulmonary hypertension.
PubMed:
A potential kairomone stimulates pheromone-responsive receptor neurons inUtetheisa ornatrix (Lepidoptera: Arctiidae).
PubMed:
Dual role of pyrrolizidine alkaloids in nectar.
PubMed:
The in vivo erythrocyte micronucleus test: measurement at steady state increases assay efficiency and permits integration with toxicity studies.
PubMed:
Bioactivation and detoxication of the pyrrolizidine alkaloid senecionine by cytochrome P-450 enzymes in rat liver.
PubMed:
Evaluation of amino acids, B vitamins and butylated hydroxyanisole as protective agents against pyrrolizidine alkaloid toxicity in rats.
PubMed:
Protective role of dietary butylated hydroxyanisole against chemical-induced acute liver damage in mice.
PubMed:
Effect of dietary Senecio jacobaea and injected Senecio alkaloids and monocrotaline on guinea pigs.
PubMed:
Effects of monocrotaline pretreatment of rats on removal of 5-hydroxytryptamine and noradrenaline by perfused lung.