Norspermidine

Norspermidine
IUPAC name N-(3-aminopropyl)propane-1,3-diamine
Other names 3,3'-diaminodipropylamine bis-(3-aminopropyl)amine dipropylenetriamine norspermidine Caldine
Identifiers
CAS number	56-18-8 Y
ChEMBL	CHEMBL28743 N
Jmol-3D images	Image 1
SMILES C(CN)CNCCCN
Properties
Molecular formula	C6H17N3
Molar mass	131.22 g/mol
Appearance	Clear, colorless liquid
Density	0.9380 g/cm³, liquid
Melting point	−14 °C, 259 K, 7 °F
Boiling point	235 °C, 508 K, 455 °F
Hazards
MSDS	Norspermidine MSDS
Flash point	118 °C (244.4 °F)
Autoignition temperature	280 °C (536 °F)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. PMC 1055875. PMID 16666576. ISSN: 0032-0889. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1055875. 
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. PMID 7096289. ISSN: 0021-924X. 
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. PMID 3255245.