Norspermidine

Norspermidine

Identifiers
CAS Number	56-18-8
3DMet	B00581
Beilstein Reference	1071254
ChEBI	CHEBI:16841
ChEMBL	ChEMBL28743
ChemSpider	5729
EC Number	200-261-2
Gmelin Reference	26839
Jmol interactive 3D	Image
KEGG	C03375
MeSH	norspermidine
PubChem	5942
RTECS number	JL9450000
UN number	2269
InChI InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2Template:Chemspidericite Key: OTBHHUPVCYLGQO-UHFFFAOYSA-NTemplate:Chemspidericite
SMILES NCCCNCCCN
Properties
Chemical formula	C6H17N3
Molar mass	131.22 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
EU classification (DSD)	T+ C
R-phrases	R22, R24, R26, R35, R43
S-phrases	(S1/2), S26, S36/37/39
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).
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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 be a natural product in humans as spermidine is.

Norspermidine is being researched for its use as an antitumor medicine in cancer treatment.^[5][6]

References

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.