Basic information
- CAS
643-20-9- Standard SMILES
C1CC2CCCN2C1- InChIKey
ADRDEXBBJTUCND-UHFFFAOYSA-N- Molecular formula
- C7H13N
- Average molar mass
- 111.18 g/mol
- Monoisotopic mass
- 111.10479942
Overview
Pyrrolizidine is a bicyclic organonitrogen heterocyclic compound comprised of two ortho-fused pyrrolidine rings which share a common nitrogen atom. It is an organic heterobicyclic compound and an organonitrogen heterocyclic compound.
Names & identifiers
- Preferred name
- Pyrrolizidine
- IUPAC
- 2,3,5,6,7,8-hexahydro-1H-pyrrolizine
- English name
- Hexahydro-1H-pyrrolizine
- Molecular formula
- C7H13N
- Molecular weight
- 111.18
Names & synonyms
PYRROLIZIDINE643-20-9HexahydropyrrolizineHexahydro-1H-pyrrolizine1H-Pyrrolizine, hexahydro-2,3,5,6,7,8-hexahydro-1H-pyrrolizine1-Azabicyclo(3.3.0)octane1-Azabicyclo[3.3.0]octaneUNII-U81KWZ2JKNU81KWZ2JKNHSDB 4300NSC 90874
Show more names
NSC-90874PYRROLIZIDINE [HSDB]CHEBI:64950DTXSID00214524NSC-1450601HPyrrolizine, hexahydroRefChem:1779301Azabicyclo(3.3.0)octane
Database identifiers
- CAS
643-20-9- PubChem CID
- 12558
- DTXSID
DTXSID00214524- ChEBI
CHEBI:64950- UNII
- U81KWZ2JKN
- EC Number
- 613-574-8
- Nikkaji
- J110.405E
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 3.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 80.4
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Toxins
Physicochemical properties
- Boiling point
- 198.35 °C · 198.35°C (rough estimate)
- Density
- 0.8928 · 0.8928 (rough estimate)
- refractive index
- 1.4731 · 1.4731 (estimate)
- FDA UNII
- 81 KWZ2JKN · U81KWZ2JKN
- Hazardous Substances Data
- 643 · 643-20-9(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards Summary
Emergency treatment: Plants- pyrrolizidine alkaloids; Pyrrolizidine alkaloids (PAs) cause veno-occlusive liver disease. Diagnosis is difficult because symptoms may be delayed for days or weeks. After drinking herbal tea or eating plants contaminated with seeds of PA plants, symptoms may include vomiting, abdominal pain, hepatomegaly, and later cirrhosis and ascites. Jaundice may be present. Children may appear to have Reye's syndrome. [HSDB] Plants containing significant amounts of pyrrolizidine alkaloids are found all over the world, comprising about 3% of all flowering plants. They have long been known to be toxic to livestock. Outbreaks of poisoning cases in humans after food contamination have been reported, and the problem is endemic in some central Asian republics. [Reference #1] Teas containing PAs include coltsfoot, comfrey, gordolobo, groundsel, mate, tansy ragwort, and T'u-san-chi. The teas may be prescribed as herbal remedies for anxiety or amenorrhea. The alkaloid is concentrated in the root of the plants. As little as 85 mg may be toxic. [Haddad, p. 1082] Over 6000 plants produce pyyrolizidine alkaloids, some of which are toxic. This is probably the most common plant toxin, and it affects livestock, wildlife, and humans. [Haddad, p. 494] Mechanism of toxicity is the metabolic conversion into pyrroles that act as alkylating agents. Hepatic disease leads to cirrhosis and possibly increased risk for hepatic carcinoma. Most poisoning cases have resulted from contamination of food grain with the seeds containing the alkaloid or from medicinal herbs. An estimated 20% of patients die, 50% recover completely, and 30% develop chronic hepatic veno-occlusive disease. [Goldfrank, p. 647, 1546]
Atmospheric Standards
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Xylenes is included on this list.
Toxicology
Chemistry & industry
Uses & manufacturing
UsesNot commercially produced in the US; [HSDB]
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Suppliers2 total
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
南京合巨药业有限公司025-57027686 17372956142 · [email protected]
Additional notes
DefinitionChEBI: A bicyclic organonitrogen heterocyclic compound comprised of two ortho-fused pyrrolidine rings which share a common nitrogen atom.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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