Spermine

Spermine
IUPAC name N,N'-bis(3-aminopropyl)butane-1,4-diamine
Other names Gerontine Musculamine Neuridine
Identifiers
CAS number	71-44-3 Y
PubChem	1103
DrugBank	DB00127
MeSH	Spermine
ChEMBL	CHEMBL23194 N
IUPHAR ligand	710
Jmol-3D images	Image 1
SMILES C(CCNCCCN)CNCCCN
Properties
Molecular formula	C10H26N4
Molar mass	202.34 g/mol
Density	0.937 g/cm3
Melting point	29 °C
Boiling point	130 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, in particular, in viruses.

Crystals of spermine phosphate were first described in 1678, in human semen, by Anton van Leeuwenhoek^[1]. The name spermin was first used by the German chemists Ladenburg and Abel in 1888^[2], and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)^[3] and Germany (by Wrede et al.)^[4].

See also

• Spermidine
• Putrescine
• Cadaverine

References

1. ^ Leeuwenhoek, A. van (1678) Observationes D. Anthonii Leeuwenhoek, de natis e semine genitali animalculis. Letter dated November 1677. Philos. Trans. Roy. Soc. London, 12,1040-1043.
2. ^ Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
3. ^ Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
4. ^ Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24

Further reading

• Slocum, R. D., Flores, H. E., "Biochemistry and Physiology of Polyamines in Plants", CRC Press, 1991, USA, ISBN 0-8493-6865-0
• Uriel Bachrach, "The Physiology of Polyamines", CRC Press, 1989, USA, ISBN 0-8493-6808-1