Spermidine
Title: Spermidine
CAS Registry Number: 124-20-9
CAS Name: N-(3-Aminopropyl)-1,4-butanediamine
Additional Names: 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.

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