8145. Reserpine
Nomenclature
Description and references
Indole alkaloid found in Rauwolfia spp. Isoln from the roots of Rauwolfia serpentina L. Benth., Apocynaceae: J. M. Müller et al., Experientia 8, 338 (1952); and structural studies: L. Dorfman et al., Helv. Chim. Acta 37, 59 (1954); N. Neuss et al., J. Am. Chem. Soc. 76, 2463 (1954). Stereochemistry: P. E. Aldrich et al., ibid. 81, 2481 (1959); Y. Ban, O. Yonemitsu, Tetrahedron 20, 2877 (1964). First total synthesis: R. B. Woodward et al., J. Am. Chem. Soc. 78, 2023 (1956); eidem, Tetrahedron 2, 1 (1958). Review of total syntheses: F.-E. Chen, J. Huang, Chem. Rev. 105, 4671-4706 (2005). 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). [α]D23 -118° (CHCl3); [α]D26 -164° (c = 0.96 in pyridine); [α]D26 -168° (c = 0.624 in DMF). uv max (CHCl3): 216, 267, 295 nm (ε 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.Derivative
Hydrochloride hydrate.Properties
Crystals, dec 224°.Caution
Reserpine is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-228.Therapeutic Category
Antihypertensive.
Therapeutic Category (Veterinary)
Hypotensive, tranquilizer. Has been used to prevent aortic rupture in turkeys.Keywords
Antihypertensive; Reserpine Derivatives