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'''Norspermidine''' is a [[polyamine]] of formula NH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-NH-CH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-NH<sub>2</sub>. Also called 3,3'-Iminodipropylamine.
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | Norspermidine
|-
| align="center" colspan="2" | [[Image:Norspermidine.PNG|350px|Norspermidine]]
|-
! {{chembox header}} | General
|-
| [[IUPAC nomenclature|Systematic name]]
| N-(3-aminopropyl)propane-1,3-diamine
|-
| Other names
| 3,3'-diaminodipropylamine<br>bis-(3-aminopropyl)amine<br>dipropylenetriamine<br>norspermidine<br>Caldine
|-
| [[Chemical formula|Molecular formula]]
| C<sub>6</sub>H<sub>17</sub>N<sub>3</sub>
|-
| [[Simplified molecular input line entry specification|SMILES]]
| C(CN)CNCCCN
|-
| [[International Chemical Identifier|InChI]]
| 1/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2
|-
| [[Molar mass]]
| 131.22 g/mol
|-
| Appearance
| Clear, colorless liquid
|-
| [[CAS registry number|CAS number]]
| 56-18-8
|-
| [[PubChem|PubChem ID]]
| 5942
|-
! {{chembox header}} | Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| 0.9380 g/cm³, liquid
|-
| [[Melting point]]
| −14 °C (7 °F)
|-
| [[Boiling point]]
| 235 °C (455 °F) (at 760 mmHg)
|-
! {{chembox header}} | Hazards
|-
| [[Material safety data sheet|MSDS]]
| [[Norspermidine#External links|External MSDS]]
|-
| [[NFPA 704]]
| {{NFPA 704 | Health = 3 | Flammability = 2 | Reactivity = 0}}
|-
| [[Flash point]]
| 118 °C (244.4 °F)
|-
| [[Autoignition temperature]]
| 280 °C (536 °F)
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25°C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

'''Norspermidine''' is a [[homologue]] of [[spermidine]]. While norspermidine has been found to occur naturally in some species of plants{{Ref|Rodriguez}}{{Ref|Hamana1}}, bacteria{{Ref|Yamamoto}}, and algae{{Ref|Hamana2}}, 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{{Ref|Prakash}}{{Ref|Sunkara}}.

==References==
#{{Note|Rodriguez}}{{cite journal
| author = Rodriguez-Garay, B ''et al''
| title = Detection of Norspermidine and Norspermine in Medicago sativa L. (Alfalfa)
| journal = Plant Physiology
| volume = 89
| issue =
| pages = 525-529
| date = 1989
| id = ISSN: 0032-0889
}}
#{{Note|Hamana1}}{{cite journal
| author = Hamana, K ''et al''
| title = Unusual polyamines in aquatic plants: the occurrence of homospermidine, norspermidine, thermospermine, norspermine, aminopropylhomospermidine, bis(aminopropyl)ethanediamine, and methylspermidine
| journal = Can. J. Bot.
| volume = 76
| issue = 1
| pages = 130–133
| date = 1998
| doi = 10.1139/cjb-76-1-130
}}
#{{Note|Yamamoto}}{{cite journal
| author = Yamamoto, S ''et al''
| title = Occurrence of norspermidine in some species of genera Vibrio and Beneckea
| journal = Biochem Biophys Res Commun.
| volume = 87
| issue = 4
| pages = 1102-1108
| date = Apr. 27, 1979
| pmid = 313792
}}
#{{Note|Hamana2}}{{cite journal
| author = Hamana, K; Matsuzaki
| title = Widespread Occurrence of Norspermidine and Norspermine in Eukaryotic Algae
| journal = J. Biochem
| volume = 91
| issue = 4
| pages = 1321-1328
| date = 1982
| id = ISSN: 0021-924X
}}
#{{Note|Prakash}}{{cite journal
| author = Prakash, NJ ''et al''
| title = Antitumor activity of norspermidine, a structural homologue of the natural polyamine spermidine
| journal = Anticancer Res.
| volume = 8
| issue = 4
| pages = 563-568
| date = 1988
| pmid = 3140710
}}
#{{Note|Sunkara}}{{cite journal
| author = Sunkara, PS ''et al''
| title = Mechanism of antitumor activity of norspermidine, a structural homologue of spermidine
| journal = Adv Exp Med Biol.
| volume = 250
| issue =
| pages = 707-716
| date = 1988
| pmid = 3255245
}}

==External links==
* [https://fscimage.fishersci.com/msds/30009.htm Norspermidine MSDS]


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Revision as of 22:39, 7 August 2007

Norspermidine
Norspermidine
General
Systematic name N-(3-aminopropyl)propane-1,3-diamine
Other names 3,3'-diaminodipropylamine
bis-(3-aminopropyl)amine
dipropylenetriamine
norspermidine
Caldine
Molecular formula C6H17N3
SMILES C(CN)CNCCCN
InChI 1/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2
Molar mass 131.22 g/mol
Appearance Clear, colorless liquid
CAS number 56-18-8
PubChem ID 5942
Properties
Density and phase 0.9380 g/cm³, liquid
Melting point −14 °C (7 °F)
Boiling point 235 °C (455 °F) (at 760 mmHg)
Hazards
MSDS External MSDS
NFPA 704
NFPA 704
safety square
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
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 homologue of 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: 525–529. ISSN: 0032-0889. {{cite journal}}: Explicit use of et al. in: |author= (help)
  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. {{cite journal}}: Explicit use of et al. in: |author= (help)
  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. PMID 313792. {{cite journal}}: Check date values in: |date= (help); Explicit use of et al. in: |author= (help)
  4. ^ Hamana, K; Matsuzaki (1982). "Widespread Occurrence of Norspermidine and Norspermine in Eukaryotic Algae". J. Biochem. 91 (4): 1321–1328. ISSN: 0021-924X.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. {{cite journal}}: Explicit use of et al. in: |author= (help)
  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. {{cite journal}}: Explicit use of et al. in: |author= (help)


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