Norspermidine

Chemical compound From Wikipedia, the free encyclopedia

Norspermidine is a polyamine of similar structure to the more common spermidine. Norspermidine has been found to occur naturally in some species of plants,[1][2] bacteria,[3] and algae.[4]

Quick facts Names, Identifiers ...
Norspermidine
Skeletal formula of norspermidine
Skeletal formula of norspermidine
Ball-and-stick model of the norspermidine molecule
Names
Preferred IUPAC name
N1-(3-Aminopropyl)propane-1,3-diamine
Identifiers
3D model (JSmol)
1071254
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.238 Edit this at Wikidata
EC Number
  • 200-261-2
26839
KEGG
MeSH norspermidine
RTECS number
  • JL9450000
UNII
UN number 2269
  • InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2 checkY
    Key: OTBHHUPVCYLGQO-UHFFFAOYSA-N checkY
  • NCCCNCCCN
Properties
C6H17N3
Molar mass 131.223 g·mol−1
Appearance Colorless liquid
Odor Ichtyal, ammoniacal
Density 938 mg mL−1
Melting point −16 to 0 °C; 3 to 32 °F; 257 to 273 K
Boiling point 240.60 °C; 465.08 °F; 513.75 K
log P −0.826
1.481–1.482
Hazards
GHS labelling:
GHS05: Corrosive GHS06: Toxic
Danger
H302, H311, H314, H317, H330
P260, P280, P284, P305+P351+P338, P310
Flash point 117 °C (243 °F; 390 K)
280 °C (536 °F; 553 K)
Lethal dose or concentration (LD, LC):
738 mg kg−1 (oral, rat)
Safety data sheet (SDS) fishersci.com
Related compounds
Related amines
Related compounds
 Agmatine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Close

Norspermidine is being researched for use as a cancer medication.[5][6]

Biosynthesis

Norspermidine is an aliphatic polyamine. In ϵ-proteobacteria, which are found in human gut microbiota, a combination of two enzymes is used to produce norspermidine from 1,3-diaminopropane.[7] First, carboxynorspermidine synthase catalyses a reductive amination using nicotinamide adenine dinucleotide phosphate (NADPH) as the reducing agent.[8][9]

2D representation of the chemical structure of 1,3-Diaminopropane.
1,3-diaminopropane
+ NADPH +
 
2D representation of the chemical structure of L-Aspartic-4-semialdehyde.
L-aspartic-4-semialdehyde
 
H+
H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27135684.
carboxynorspermidine
+ NADP+
 

The intermediate, carboxynorspermidine, is then decarboxylated by carboxynorspermidine decarboxylase:[7][9]

2D representation of the chemical structure of Q27135684.
carboxynorspermidine
 
 
CO2
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of norspermidine .
norspermidine

References

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