Title: Spermidine
CAS Registry Number: 124-20-9
CAS Name: N-(3-Aminopropyl)-1,4-butanediamine
Synonyms: N-(g-aminopropyl)tetramethylenediamine
Molecular Formula: C7H19N3
Molecular Weight: 145.25
Percent Composition: C 57.88%, H 13.18%, N 28.93%
Line Formula: NH2(CH2)4NH(CH2)3NH2
Literature References: Biogenic polyamine formed from putrescine; a precursor of spermine,
q.q.v. First detected in human sperm, but occurs widely in nature. Essential for both normal and neoplastic tissue growth. Synthesis: H. W. Dudley
et al., Biochem. J. 20, 1082 (1926);
21, 97 (1927); J. V. Braun, W. Pinkernelle,
Ber. 70, 1234 (1937); M. Danzig, H. P. Schultz,
J. Am. Chem. Soc. 74, 1836 (1952). For reviews of the early literature,
see M. Guggenheim,
Die biogenen Amine (S. Karger, Basel, 4th ed., 1951) 619 pp; H. Tabor
et al., Annu. Rev. Biochem. 30, 579-604 (1961). Role in cell growth processes: C. W. Tabor, H. Tabor,
ibid. 45, 285 (1976); J. Janne
et al., Biochim. Biophys. Acta 473, 241 (1978); C. W. Porter, R. J. Bergeron,
Science 219, 1083 (1983). Formation and interconversion of spermidine and putrescine in mammalian cells: A. E. Pegg
et al., Adv. Enzyme Regul. 19, 427 (1980). Effect on polypeptide chain elongation
in vitro: A. K. Abraham, A. Pihl,
Eur. J. Biochem. 106, 257 (1980). Regulation of tRNA methyltransferase activity: M. Mach
et al., Biochem. J. 202, 153 (1982). HPLC study: C. E. Prussak, D. H. Russell,
J. Chromatogr. 229, 47 (1982). Interaction with actin,
q.v.: C. Oriol-Audit,
Biochem. Biophys. Res. Commun. 105, 1096 (1982). Studies on use as a biochemical tool in cancer research: A. Thyss
et al., Eur. J. Cancer Clin. Oncol. 18, 611 (1982); V. Quemener
et al., J. Nat. Prod. 45, 608 (1982); C. W. Porter
et al., Cancer Res. 42, 4072 (1982). Toxicity study: P. R. Langford
et al., J. Antibiot. 35, 1387 (1982).
Reviews: T. C. Theoharides,
Life Sci. 27, 703-713 (1980); O. Heby,
Differentiation 19, 1-20 (1981); L. Stevens,
Med. Biol. 59, 308-313 (1981). Book:
Polyamines in Biology and Medicine, D. R. Morris, L. J. Marton, Eds. (Dekker, New York, 1981) 512 pp.
Properties: Liq, bp14 128-130°. Sol in water, ethanol, ether.
Boiling point: bp14 128-130°
Derivative Type: Trihydrochloride
Molecular Formula: C7H22Cl3N3
Molecular Weight: 254.63
Percent Composition: C 33.02%, H 8.71%, Cl 41.77%, N 16.50%
Properties: Cryst from ethanolic HCl (65:2). mp 256-258°.
Melting point: mp 256-258°
Use: As a tool in biochemical research.