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Spermine

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Spermine
Names
IUPAC name N,N'-bis(3-aminopropyl)butane-1,4-diamine
Other names Gerontine
Musculamine
Neuridine
Identifiers
CAS Number
3D model (JSmol)
DrugBank
ECHA InfoCard 100.000.686 Edit this at Wikidata
IUPHAR/BPS
MeSH Spermine
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • C(CCNCCCN)CNCCCN
Properties
Chemical formula C10H26N4
Molar mass 202.34 g/mol
Density 0.937 g/cm
Melting point 29 °C
Boiling point 130 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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.).

See also

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


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