Description and references

Indole alkaloid with α₂-adrenergic blocking activity. Found in Corynanthe johimbe K. Schum., Rubiaceae and related trees, also in Rauwolfia serpentina (L.) Benth., Apocynaceae: Raymond-Hamet, J. Pharm. Chim. 19, 209 (1934); Hofmann, Helv. Chim. Acta 37, 849 (1954); Stoll, Jucker, Ullmanns Encyklopdie der technischen Chemie vol. 3 (Munich, 3rd ed., 1953) p 266; Bader et al., J. Am. Chem. Soc. 76, 1695 (1954). Structure: Witkop, Ann. 554, 83 (1943); Clemo, Swan, J. Chem. Soc. 1946, 617. Stereochemistry: Janot et al., Bull. Soc. Chim. Fr. 1952, 1085; Godfredsen, Vandegal, Acta Chem. Scand. 10, 1414 (1956); Van Tamelen et al., J. Am. Chem. Soc. 78, 4628 (1956); Ban, Yonemitsu, Tetrahedron 20, 2877 (1964). Synthesis: Van Tamelen et al., J. Am. Chem. Soc. 80, 5006 (1958); Liljegren, Potts, J. Org. Chem. 27, 377 (1962). Total synthesis: Van Tamelen et al., J. Am. Chem. Soc. 91, 7315 (1969); Stork, Guthikonda, ibid. 94, 5109 (1972); T. Kametani et al., Chem. Pharm. Bull. 24, 2500 (1976); E. Wenkert et al., J. Am. Chem. Soc. 100, 4894 (1978); 101, 5370 (1979); 104, 2244 (1982); I. Ninomiya et al., Heterocycles 14, 631 (1980). Pharmacokinetics in humans: J. A. Owen et al., Eur. J. Clin. Pharmacol. 32, 577 (1987). Clinical studies in impotence: K. Reid et al., Lancet 2, 421 (1987); A. Morales et al., J. Urol. 137, 1168 (1987). Review of pharmacology and use in molecular studies of α₂-adrenoreceptor: M. R. Goldberg, D. Robertson, Pharmacol. Rev. 35, 143-180 (1987). Comprehensive description: A. G. Mekkawi, A. A. Al-Badr, Anal. Profiles Drug Subs. 16, 731-768 (1986).

Properties

Derivative