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Pyrrolizidine information


Pyrrolizidine
Names
Preferred IUPAC name
Hexahydro-1H-pyrrolizine
Other names
Hexahydropyrrolizine
1-Azabicyclo[3.3.0]octane
Identifiers
CAS Number
  • 643-20-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 12039 checkY
ECHA InfoCard 100.117.254 Edit this at Wikidata
PubChem CID
  • 12558
UNII
  • U81KWZ2JKN checkY
CompTox Dashboard (EPA)
  • DTXSID00214524 Edit this at Wikidata
InChI
  • InChI=1S/C7H13N/c1-3-7-4-2-6-8(7)5-1/h7H,1-6H2 checkY
    Key: ADRDEXBBJTUCND-UHFFFAOYSA-N checkY
  • InChI=1/C7H13N/c1-3-7-4-2-6-8(7)5-1/h7H,1-6H2
    Key: ADRDEXBBJTUCND-UHFFFAOYAT
SMILES
  • N12CCCC1CCC2
Properties
Chemical formula
C7H13N
Molar mass 111.188 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyrrolizidine is a heterocyclic organic compound. Formally, it is a saturated derivative of pyrrolizine.

Pyrrolizidine forms the central chemical structure of a variety of alkaloids known collectively as pyrrolizidine alkaloids.[1] It is one of five classes of iminosugars. These are often synthesized from a carbohydrate.[2]

  1. ^ Pyrrolizidine alkaloids at KEGG Archived 2016-03-03 at the Wayback Machine
  2. ^ Lauritsen, Anne; Madsen, Robert (2006-07-19). "Synthesis of naturally occurring iminosugars from D-fructose by the use of a zinc-mediated fragmentation reaction". Organic & Biomolecular Chemistry. 4 (15): 2898–2905. doi:10.1039/B605818C. ISSN 1477-0539. PMID 16855738.

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Heliotropium

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species are weeds, and many are hepatotoxic if eaten due to abundant pyrrolizidine alkaloids. There have been cases of canine death due to over-ingestion...

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Symphytum

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including allantoin, mucilage, saponins, tannins, pyrrolizidine alkaloids, and inulin, among others. Pyrrolizidine alkaloids are responsible for comfrey's hepatotoxicity...

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Farfugium japonicum

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protection from cold winds. Farfugium japonicum contains tumorigenic pyrrolizidine alkaloids. cv. 'Argenteum' Flowers "Leopard Plant". Home & Garden Information...

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Symphytum officinale

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toxicity. Comfrey is mildly toxic. Like most Boraginaceae, it contains pyrrolizidine alkaloids which are toxic compounds readily absorbed via the stomach...

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Senecio vulgaris

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the cinnabar moth larvae respond (get excited) specifically to the pyrrolizidine alkaloids, which all Senecio contain. Moths and caterpillars Cinnabar...

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Borage seed oil

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not better than placebo when taken orally. Borage oil may contain the pyrrolizidine alkaloid amabiline, which is hepatotoxic leading to a risk of liver...

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Petasites japonicus

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in order to make namul. Like other Petasites species, fuki contains pyrrolizidine alkaloids (PAs) which have been associated with cumulative damage to...

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Echium vulgare

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the plant is toxic to horses and cattle through the accumulation of pyrrolizidine alkaloids in the liver. It is a biennial or monocarpic perennial plant...

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Eupatorium serotinum

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late-season nectar for Monarch Butterflies. There is also evidence that pyrrolizidine alkaloids produced by Eupatorium serotinum are beneficial to Monarchs...

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Ageratum conyzoides

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of contamination of grain with A. conyzoides. The plant contains the pyrrolizidine alkaloids lycopsamine and echinatine. A. conyzoides is prone to becoming...

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Jacobaea vulgaris

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which can cause compositae dermatitis. These are different from the pyrrolizidine alkaloids which are responsible for the toxic effects. Honey collected...

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Cynoglossum officinale

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worst weeds in the state. Cynoglossum officinale contains tumorigenic pyrrolizidine alkaloids. It is toxic to cows and is especially dangerous to pasture...

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Estigmene acrea

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clovers, and maize. The moth does not seem to be affected by any type of pyrrolizidine alkaloid present in many plant families, including the borage, legume...

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Heliotropium indicum

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leaves are used as poultice. Heliotropium indicum contains tumorigenic pyrrolizidine alkaloids. "Trompang elepante". Philippine Medicinal Plants oten. "Heliotropium...

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Pyrrolizidine alkaloid sequestration by insects is a strategy to facilitate defense and mating. Various species of insects have been known to use molecular...

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Creatonotos gangis

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a dietary supplement. Concerns about the potential toxic effects of pyrrolizidine alkaloids in butterbur limit its use in human and animal studies. Butterbur...

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Eupatorium cannabinum

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