Norspermidine

Norspermidine
Names
	Preferred IUPAC name N1-(3-Aminopropyl)propane-1,3-diamine
Identifiers
CAS Number	56-18-8 ;
3D model (JSmol)	Interactive image;
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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H314, H317, H330
Precautionary statements	P260, P280, P284, P305+P351+P338, 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)
Safety data sheet (SDS)	fishersci.com
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.

[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.

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Names


Preferred IUPAC name N¹-(3-Aminopropyl)propane-1,3-diamine
Identifiers
CAS Number	56-18-8^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1071254
ChEBI	CHEBI:16841^N
ChEMBL	ChEMBL28743^N
ChemSpider	5729^N
ECHA InfoCard	100.000.238
EC Number	200-261-2
Gmelin Reference	26839
KEGG	C03375^N
MeSH	norspermidine
PubChem CID	5942
RTECS number	JL9450000
UNII	RN1144MGND^Y
UN number	2269
CompTox Dashboard (EPA)	DTXSID0025440
InChI InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2^Y Key: OTBHHUPVCYLGQO-UHFFFAOYSA-N^Y
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 (n_D)	1.481–1.482
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H314, H317, H330
Precautionary statements	P260, P280, P284, P305+P351+P338, 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)
Safety data sheet (SDS)	fishersci.com
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). N verify (what is ^YN ?) Infobox references