Norspermidine

Norspermidine
	Skeletal formula of 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). Infobox references

Norspermidine is a polyamine of similar structure to the more common spermidine. Norspermidine has been found to occur naturally in some species of plants,^[1]^[2] bacteria,^[3] and algae.^[4]

Norspermidine is being researched for use as a cancer medication.^[5]^[6]

Biosynthesis

Norspermidine is an aliphatic polyamine. In ϵ-proteobacteria, which are found in human gut microbiota, a combination of two enzymes is used to produce norspermidine from 1,3-diaminopropane.^[7] First, carboxynorspermidine synthase catalyses a reductive amination using nicotinamide adenine dinucleotide phosphate (NADPH) as the reducing agent.^[8]^[9]

1,3-diaminopropane

+ NADPH +

L-aspartic-4-semialdehyde

H⁺

H₂O

Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right

2D representation of the chemical structure of Q27135684.

carboxynorspermidine

+ NADP⁺

The intermediate, carboxynorspermidine, is then decarboxylated by carboxynorspermidine decarboxylase:^[7]^[9]

carboxynorspermidine

CO₂

Rightward reaction arrow with minor product(s) to top right

norspermidine

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. doi:10.1093/oxfordjournals.jbchem.a133818. 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". Progress in Polyamine Research. Adv Exp Med Biol. Vol. 250. pp. 707–716. doi:10.1007/978-1-4684-5637-0_62. ISBN 978-1-4684-5639-4. PMID 3255245.
^ ^a ^b Hanfrey CC, Pearson BM, Hazeldine S, Lee J, Gaskin DJ, Woster PM, Phillips MA, Michael AJ (December 2011). "Alternative spermidine biosynthetic route is critical for growth of Campylobacter jejuni and is the dominant polyamine pathway in human gut microbiota". The Journal of Biological Chemistry. 286 (50): 43301–12. doi:10.1074/jbc.M111.307835. PMC 3234850. PMID 22025614.
^ Nakao H, Shinoda S, Yamamoto S (July 1991). "Purification and some properties of carboxynorspermidine synthase participating in a novel biosynthetic pathway for norspermidine in Vibrio alginolyticus". Journal of General Microbiology. 137 (7): 1737–42. doi:10.1099/00221287-137-7-1737. PMID 1955861.
^ ^a ^b Lee J, Sperandio V, Frantz DE, Longgood J, Camilli A, Phillips MA, Michael AJ (April 2009). "An alternative polyamine biosynthetic pathway is widespread in bacteria and essential for biofilm formation in Vibrio cholerae". The Journal of Biological Chemistry. 284 (15): 9899–907. doi:10.1074/jbc.M900110200. PMC 2665113. PMID 19196710.

[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. doi:10.1093/oxfordjournals.jbchem.a133818. 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". Progress in Polyamine Research. Adv Exp Med Biol. Vol. 250. pp. 707–716. doi:10.1007/978-1-4684-5637-0_62. ISBN 978-1-4684-5639-4. PMID 3255245.

[Hanfrey-7] Hanfrey CC, Pearson BM, Hazeldine S, Lee J, Gaskin DJ, Woster PM, Phillips MA, Michael AJ (December 2011). "Alternative spermidine biosynthetic route is critical for growth of Campylobacter jejuni and is the dominant polyamine pathway in human gut microbiota". The Journal of Biological Chemistry. 286 (50): 43301–12. doi:10.1074/jbc.M111.307835. PMC 3234850. PMID 22025614.

[8] Nakao H, Shinoda S, Yamamoto S (July 1991). "Purification and some properties of carboxynorspermidine synthase participating in a novel biosynthetic pathway for norspermidine in Vibrio alginolyticus". Journal of General Microbiology. 137 (7): 1737–42. doi:10.1099/00221287-137-7-1737. PMID 1955861.

[Lee-9] Lee J, Sperandio V, Frantz DE, Longgood J, Camilli A, Phillips MA, Michael AJ (April 2009). "An alternative polyamine biosynthetic pathway is widespread in bacteria and essential for biofilm formation in Vibrio cholerae". The Journal of Biological Chemistry. 284 (15): 9899–907. doi:10.1074/jbc.M900110200. PMC 2665113. PMID 19196710.

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