Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H13N |
| Molecular Weight | 111.1848 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CC2CCCN2C1
InChI
InChIKey=ADRDEXBBJTUCND-UHFFFAOYSA-N
InChI=1S/C7H13N/c1-3-7-4-2-6-8(7)5-1/h7H,1-6H2
| Molecular Formula | C7H13N |
| Molecular Weight | 111.1848 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Pyrrolizidine is a heterocyclic organic compound, that forms the central chemical structure of a variety of alkaloids known collectively as pyrrolizidine alkaloids. Pyrrolizidine alkaloids are found in 14 plant families, as well as in animal organisms. Some Pyrrolizidine alkaloids are used in medicine. The greatest value among them are platifillin and sarratsin contained in the plants of the genus Baptismal (Senecio). Pyrrolizidine is a tertiary amine, which easily forms salts and quaternary ammonium bases, for example, tetrachloroaurate, hexachloroplatinate, picrate, iodomethyl. Pyrrolizidine is obtained by the action of concentrated sulfuric acid on N-bromo-2-pro-pyrrolidine.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants. | 2003-08 |
|
| Retrorsine: a kinetic study of its influence on rat liver regeneration in the portal branch ligation model. | 2003-07 |
|
| Life history parameters of the two-spotted spider mite (Tetranychus urticae Koch) feeding on bean leaves treated with pyrrolizidine alkaloids. | 2003-06-10 |
|
| [Proliferation of retrorsine-treated SD rat immortalized hepatocytes after intrasplenic transplantation]. | 2003-06 |
|
| Gender differences in microsomal metabolic activation of hepatotoxic clivorine in rat. | 2003-06 |
|
| Dichloroketene-chiral olefin-based approach to pyrrolizidines: highly stereocontrolled synthesis of (+)-amphorogynine A. | 2003-05-15 |
|
| Synthesis of novel 1H-pyrrolizine-5-carboxamides and their antimicrobial properties. | 2003-05 |
|
| Toxicology and carcinogenesis studies of riddelliine (CAS No. 23246-96-0) in F344/N rats and B6C3F1 mice (gavage studies). | 2003-05 |
|
| Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. | 2003-05 |
|
| Alkaloid profile of Bulgarian species from genus Senecio L. | 2003-04-25 |
|
| Pyrrolizidine alkaloids from Lithospermum canescens Lehm. | 2003-04-25 |
|
| Correlation of DNA adduct formation and riddelliine-induced liver tumorigenesis in F344 rats and B6C3F(1) mice. | 2003-04-25 |
|
| Molecular evolution by change of function. Alkaloid-specific homospermidine synthase retained all properties of deoxyhypusine synthase except binding the eIF5A precursor protein. | 2003-04-11 |
|
| [The common butterbur (Petasites hybridus)--portrait of a medicinal herb]. | 2003-04 |
|
| Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue. | 2003-03-07 |
|
| Toxicity of Senecio vernalis to laying hens and evaluation of residues in eggs. | 2003-03 |
|
| Role of neutrophils in the synergistic liver injury from monocrotaline and bacterial lipopolysaccharide exposure. | 2003-03 |
|
| Organoruthenium(II) and (III) amidinates, (eta5-C5Me5)Ru(eta-amidinate) and (eta5-C5Me5)RuCl(eta-amidinate), as unique redox catalysts for the intramolecular Kharasch reactions: facile access to a pyrrolizidine alkaloid skeleton under mild conditions. | 2003-02-07 |
|
| Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults. | 2003-02 |
|
| Evidence for general occurrence of homospermidine in plants and its supposed origin as by-product of deoxyhypusine synthase. | 2003-02 |
|
| Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine. | 2003-01 |
|
| Synthesis of (1R,2R,7R,7aS)-1-hydroxymethyl-2,3,5,6,7,7a-hexahydropyrrolizidine-1,2,7-triol from rosmarinine degradation. | 2003-01 |
|
| The role of Kupffer cells and TNF-alpha in monocrotaline and bacterial lipopolysaccharide-induced liver injury. | 2003-01 |
|
| Pyrrolizidine alkaloids in foods. | 2003 |
|
| [Senecio jacobaea: deceiving beauty. Senecio jacobaea poisoning]. | 2002-12-15 |
|
| UCS1025A and B, new antitumor antibiotics from the fungus Acremonium species. | 2002-12-12 |
|
| Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid. | 2002-12-10 |
|
| Pyrrolizidine alkaloids. | 2002-12 |
|
| New polyhydroxylated pyrrolidine, piperidine, and pyrrolizidine alkaloids from Scilla sibirica. | 2002-12 |
|
| Pyrrolizidine alkaloid clivorine inhibits human normal liver L-02 cells growth and activates p38 mitogen-activated protein kinase in L-02 cells. | 2002-12 |
|
| Alkaloids from the roots of Senecio macedonicus Griseb. | 2002-11-21 |
|
| The hepatic endothelial carcinogen riddelliine induces endothelial apoptosis, mitosis, S phase, and p53 and hepatocytic vascular endothelial growth factor expression after short-term exposure. | 2002-11-01 |
|
| Species differences in the in vitro metabolic activation of the hepatotoxic pyrrolizidine alkaloid clivorine. | 2002-11 |
|
| Comfrey toxicity revisited. | 2002-11 |
|
| A highly sensitive taste receptor cell for pyrrolizidine alkaloids in the lateral galeal sensillum of a polyphagous caterpillar, Estigmene acraea. | 2002-10 |
|
| Pyrrolizidine alkaloids from Senecio jacobaea affect fungal growth. | 2002-09 |
|
| Cell-specific expression of homospermidine synthase, the entry enzyme of the pyrrolizidine alkaloid pathway in Senecio vernalis, in comparison with its ancestor, deoxyhypusine synthase. | 2002-09 |
|
| Hepatic veno-occlusive disease as a result of a traditional remedy: confirmation of toxic pyrrolizidine alkaloids as the cause, using an in vitro technique. | 2002-09 |
|
| Oxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic Acid. | 2002-08-28 |
|
| A novel, stereoselective silyl-directed Stevens [1,2]-shift of ammonium ylides. | 2002-08-22 |
|
| [Budd-Chiari syndrome after herbal tea?]. | 2002-08-19 |
|
| Polyhydroxy alkaloids: chromatographic analysis. | 2002-08-16 |
|
| Heme oxygenase-1 reduces murine monocrotaline-induced pulmonary inflammatory responses and resultant right ventricular overload. | 2002-08 |
|
| Toxic pyrrolyzidine alkaloids from three mongolian plants. a possible risk for cattle poisoning. | 2002-08 |
|
| Pyrrolizidine alkaloid profiles of some Senecio species from Egypt. | 2002-07-23 |
|
| Toxicokinetics of riddelliine, a carcinogenic pyrrolizidine alkaloid, and metabolites in rats and mice. | 2002-07-15 |
|
| Liver repopulation after cell transplantation in mice treated with retrorsine and carbon tetrachloride. | 2002-06-15 |
|
| Pyrrolizidine alkaloids in Pulmonaria obscura. | 2002-05 |
|
| Heterologous expression of a bacterial homospermidine synthase gene in transgenic tobacco: effects on the polyamine pathway. | 2002-04 |
|
| Veno-occlusive disease in a fetus caused by pyrrolizidine alkaloids of food origin. | 2002-02-25 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:56:02 GMT 2025
by
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Mon Mar 31 19:56:02 GMT 2025
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| Record UNII |
U81KWZ2JKN
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| Record Status |
Validated (UNII)
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| Record Version |
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PYRROLIZIDINE
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