Norspermidine

Norspermidine
Identifiers
CAS Number	56-18-8 ;
3D model (JSmol)	Interactive image;
3DMet	B00581;
Beilstein Reference	1071254
ChEBI	CHEBI:16841 ;
ChEMBL	ChEMBL28743 ;
ChemSpider	5729 ;
ECHA InfoCard	100.000.238
EC Number	200-261-2;
Gmelin Reference	26839
KEGG	C03375 ;
MeSH	norspermidine
PubChem CID	5942;
RTECS number	JL9450000;
UNII	RN1144MGND ;
UN number	2269
CompTox Dashboard (EPA)	DTXSID0025440 ;
	InChI InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2 Key: OTBHHUPVCYLGQO-UHFFFAOYSA-N ;
	SMILES NCCCNCCCN;
Properties
Chemical formula	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
Refractive index (nD)	1.481–1.482
Hazards
Safety data sheet	fishersci.com
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H311, H314, H317, H330
GHS precautionary statements	P260, P280, P284, P305+351+338, P310
Flash point	117 °C (243 °F; 390 K)
Autoignition; temperature	280 °C (536 °F; 553 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	738 mg kg−1 (oral, rat)
Related compounds
Related amines	Dipropylamine; Methyl-n-amylnitrosamine; Spermidine;
Related compounds	Agmatine
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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]

References

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.
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.
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.
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.
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.
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.

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[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.