170442-12-3

Basic information

• Product Name: 1H-Pyrrolizin-1-amine,hexahydro-(9CI)
• Synonyms: 1H-Pyrrolizin-1-amine,hexahydro-(9CI)
• CAS NO: 170442-12-3
• Molecular Formula: C7H14N2
• Molecular Weight: 126.19946
• Product Categories: AMINEPRIMARY;AMINETERTIARY
• Mol File: 170442-12-3.mol

Chemical Properties

• Boiling Point: 160.7±8.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• PKA: 10.40±0.40(Predicted)
• CAS DataBase Reference: 1H-Pyrrolizin-1-amine,hexahydro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolizin-1-amine,hexahydro-(9CI)(170442-12-3)
• EPA Substance Registry System: 1H-Pyrrolizin-1-amine,hexahydro-(9CI)(170442-12-3)

Safety Data

• Hazardous Substances Data: 170442-12-3(Hazardous Substances Data)

Usage

Structure

Saturated heterocyclic amine with a six-membered ring and a pyrrolizine core

Type

Derivative of pyrrolizine

Usage

Building block in organic synthesis and pharmaceutical research for the production of various compounds

Potential applications

Drug development, medicinal chemistry, new materials, and chemical processes

Known as

Hexahydro-1H-pyrrolizin-1-amine

Upstream product

• 15912-22-8 (+/-)-1-hydroxyiminopyrrolizidine 

Relevant articles and documents

Ether bridge formation in loline alkaloid biosynthesis

Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lolO, resulting in the accumulation of an alkaloid identified as exo-1-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes differing in alkaloid profiles were sequenced, revealing that those with mutated lolO accumulated exo-1-acetamidopyrrolizidine but no lolines. Heterologous expression of wild-type lolO complemented a lolO mutant, resulting in the production of N-acetylnorloline. These results indicated that the non-heme iron oxygenase, LolO, is required for ether bridge formation, probably through oxidation of exo-1-acetamidopyrrolizidine.