8743. Spermine

Nomenclature

CAS number: 71-44-3
N1,N4-Bis(3-aminopropyl)-1,4-butanediamine; N,N′-bis(3-aminopropyl)tetramethylenediamine; gerontine; musculamine; neuridine.
C10H26N4; mol wt 202.34.
C 59.36%, H 12.95%, N 27.69%.

Description and references

Biogenic polyamine formed from spermidine, q.v., and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. First observed in human semen and described as the cryst phosphate salt by A. von Leeuwenhoek, Philos. Trans. R. Soc. London 12, 1040 (1678). For a description of the history, occurrence, formation, and early prepns of spermine, see Beilstein vol. IV, Suppl. 1, 704; M. Guggenheim, Die biogenen Amine (S. Karger, Basel, 4th ed., 1951) 619 pp; H. Tabor et al., Annu. Rev. Biochem. 30, 579-604 (1961). Prepn of spermine and its tetrahydrochloride: Israel et al., J. Med. Chem. 7, 710 (1964). Role in cell growth processes: C. W. Tabor, H. Tabor, Annu. Rev. Biochem. 45, 285 (1976); J. Janne et al., Biochim. Biophys. Acta 473, 241 (1978). Modulation of calcium-dependent immune processes: T. C. Theoharides, Life Sci. 27, 703 (1980). Biosynthesis in fungi: L. Stevens, Med. Biol. 59, 308 (1981). HPLC study: C. E. Prussak, D. H. Russell, J. Chromatogr. 229, 47 (1982). Use as a biochemical marker for malignant tumors: Y. Horn et al., Cancer Res. 42, 3248 (1982). Metabolic study: A. E. Pegg et al., Biochemistry 21, 5082 (1982). Review of role in cell proliferation and differentiation: O. Heby, Differentiation 19, 1-20 (1981). Book: Polyamines in Biology and Medicine D. R. Morris, L. J. Marton, Eds. (Dekker, New York, 1981) 512 pp.

Chemical structure

Properties

Needles, mp 55-60°. Liq, bp0.5 141-142°. Strong base, absorbs carbon dioxide from air. Corrosive. Keep well closed. Sol in water, lower alcohols, chloroform. Practically insol in ether, benzene, petr ether.

Derivative

Diphosphate hexahydrate.

Nomenclature

CAS number: 58298-97-8
Spermine phosphate.
C10H26N4.2H3PO4.6H2O; mol wt 506.42.
C 23.72%, H 8.76%, N 11.06%, P 12.23%, O 44.23%.

Properties

Cryst from water, mp 230-234° (dec). Soly in water: 0.037% at 20°; 1% at 100°. Insol in alc, ether and other organic solvents. Sol in dilute acids and alkali. Known as Charcot-Neumann crystals, also found in spleen, blood, bone marrow in leukemia and secretions in asthma.

Derivative

Tetrahydrochloride.

Nomenclature

CAS number: 306-67-2
C10H26N4.4HCl; mol wt 348.18.
C 34.50%, H 8.68%, N 16.09%, Cl 40.73%.

Properties

Cryst from ethanol, mp 312-314.5°.

Use

As a tool in biochemical research.