Norspermidine

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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]
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 (7 °F)

Boiling point

235 °C (455 °F) (at 760 mmHg)

Hazards
MSDS Norspermidine MSDS
Flash point 118 °C (244.4 °F)
Autoignition
temperature
280 °C (536 °F)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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].

[edit] References

  1. ^ Rodriguez-Garay, B et al (1989). "Detection of Norspermidine and Norspermine in Medicago sativa L. (Alfalfa)". Plant Physiology 89: 525–529. ISSN: 0032-0889. 
  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. 
  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.