Spermine

Spermine
Names
	Preferred IUPAC name N1,N4-Bis(3-aminopropyl)butane-1,4-diamine
Identifiers
CAS Number	71-44-3 (free base) ; 306-67-2 (tetrahydrochloride) ;
3D model (JSmol)	Interactive image;
3DMet	B01325;
Beilstein Reference	1750791
ChEBI	CHEBI:15746 ;
ChEMBL	ChEMBL23194 ;
ChemSpider	1072 ;
DrugBank	DB00127 ;
ECHA InfoCard	100.000.686
EC Number	200-754-2;
Gmelin Reference	454653
IUPHAR/BPS	710;
KEGG	C00750 ;
MeSH	Spermine
PubChem CID	1103;
RTECS number	EJ7175000;
UNII	2FZ7Y3VOQX (free base) ; 9CI1570O48 (tetrahydrochloride) ;
UN number	3259
CompTox Dashboard (EPA)	DTXSID9058781 ;
	InChI InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 Key: PFNFFQXMRSDOHW-UHFFFAOYSA-N ;
	SMILES NCCCNCCCCNCCCN;
Properties
Chemical formula	C10H26N4
Molar mass	202.346 g·mol−1
Appearance	Colourless crystals
Odor	Fishy or like that of semen
Density	917 mg mL−1
Melting point	28 to 30 °C (82 to 86 °F; 301 to 303 K)
Boiling point	150.1 °C; 302.1 °F; 423.2 K at 700 Pa
log P	−0.543
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	corrosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P280, P305+P351+P338, P310
Flash point	110 °C (230 °F; 383 K)
Related compounds
Related compounds	Spermidine, Putrescine, Cadaverine, Diethylenetriamine, Norspermidine, Thermospermine
	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

Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses. It functions as an intracellular free radical scavenger to protect DNA from free radical attack. Spermine is the chemical primarily responsible for the characteristic odor of semen.

Antonie van Leeuwenhoek first described crystals of spermine phosphate in human semen in 1678. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.).

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