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Literature References:  Found in Rauwolfia spp.  Isoln from the roots of Rauwolfia serpentina L. Benth., Apocynaceae:  J. M. M¨¹ller et al., Experientia 8, 338 (1952); Dorfman et al., Helv. Chim. Acta 37, 59 (1954); Schwyzer, Mueller, US 2833771 (1958 to Ciba).  Structure:  Dorfman et al., loc. cit.; Neuss et al., J. Am. Chem. Soc. 76, 2463 (1954).  Stereochemistry:  Diassi et al., ibid. 77, 2028, 4687 (1955); Huebner, Wenkert, ibid. 4180; van Tamelen, Hance, ibid. 4693; Aldrich et al., ibid. 81, 2481 (1959); Ban, Yonemitsu, Tetrahedron 20, 2877 (1964).  Total synthesis:  R. B. Woodward et al., J. Am. Chem. Soc. 78, 2023 (1956); eidem, Tetrahedron 2, 1-57 (1958); B. A. Pearlman, J. Am. Chem. Soc. 101, 6404 (1979); P. A. Wender et al., ibid. 102, 6157 (1980).  Stereoselective synthesis:  G. Stork, Pure Appl. Chem. 61, 439 (1989).  Comprehensive description:  R. E. Schirmer, Anal. Profiles Drug Subs. 4, 384-430 (1975).  Review:  A. Scriabine, Ed. in Pharmacology of Antihypertensive Drugs (Raven, New York, 1980) pp 119-125.  Review of carcinogenicity studies:  IARC Monographs 10, 217-229 (1976); R. M. Diener et al., Toxicol. Pathol. 8, 1-21 (1980).
Properties:  Long prisms from dil acetone, dec 264-265?(dec 277-277.5?in evac tube).  [a]D23 -118?(CHCl3); [a]D26 -164?(c = 0.96 in pyridine); [a]D26 -168?(c = 0.624 in DMF).  uv max (CHCl3):  216, 267, 295 nm (e 61700, 17000, 10200).  Weak base.  pK 6.6.  Very sparingly sol in water.  Freely sol in chloroform (~1 g/6 ml), methylene chloride, glacial acetic acid.  Sol in benzene, ethyl acetate.  Slightly sol in acetone, methanol, alcohol (1 g/1800 ml), ether, and in aq solns of acetic and citric acids.  Upon standing most solns acquire a yellow color and pronounced fluorescence; esp after the addition of acid or upon exposure to light.
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