Norspermidine

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)
3DMet
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).
☒N verify (what is checkY☒N ?)

Norspermidine is a polyamine of similar structure to the more common spermidine. While norspermidine has been found to occur naturally in some species of plants,[1][2] bacteria,[3] and algae,[4] it is not known to exist in humans.

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

  1. ^ Rodriguez-Garay, B; et al. (1989). "Detection of Norspermidine and Norspermine in Medicago sativa L. (Alfalfa)". Plant Physiology. 89 (2): 525–529. doi:10.1104/pp.89.2.525. ISSN 0032-0889. PMC 1055875. PMID 16666576.
  2. ^ Hamana, K; et al. (1998). "Unusual polyamines in aquatic plants: the occurrence of homospermidine, norspermidine, thermospermine, norspermine, aminopropylhomospermidine, bis(aminopropyl)ethanediamine, and methylspermidine". Can. J. Bot. 76 (1): 130–133. doi:10.1139/cjb-76-1-130.
  3. ^ Yamamoto, S; et al. (Apr 27, 1979). "Occurrence of norspermidine in some species of genera Vibrio and Beneckea". Biochem Biophys Res Commun. 87 (4): 1102–1108. doi:10.1016/S0006-291X(79)80021-2. PMID 313792.
  4. ^ Hamana, K; Matsuzaki, S (1982). "Widespread Occurrence of Norspermidine and Norspermine in Eukaryotic Algae". J. Biochem. 91 (4): 1321–1328. ISSN 0021-924X. PMID 7096289.
  5. ^ Prakash, NJ; et al. (1988). "Antitumor activity of norspermidine, a structural homologue of the natural polyamine spermidine". Anticancer Res. 8 (4): 563–568. PMID 3140710.
  6. ^ Sunkara, PS; et al. (1988). "Mechanism of antitumor activity of norspermidine, a structural homologue of spermidine". Adv Exp Med Biol. 250: 707–716. doi:10.1007/978-1-4684-5637-0_62. PMID 3255245.