Title: Reserpine
CAS Registry Number: 50-55-5
CAS Name: (3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
Synonyms: 3,4,5-trimethoxybenzoyl methyl reserpate
Trademarks: Rivasin (Solvay); Serpasil (Novartis)
Molecular Formula: C33H40N2O9
Molecular Weight: 608.68
Percent Composition: C 65.12%, H 6.62%, N 4.60%, O 23.66%
Literature 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). [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.
pKa: pK 6.6
Optical Rotation: [a]D23 -118° (CHCl3); [a]D26 -164° (c = 0.96 in pyridine); [a]D26 -168° (c = 0.624 in DMF)
Absorption maximum: uv max (CHCl3): 216, 267, 295 nm (e 61700, 17000, 10200)
Derivative Type: Hydrochloride hydrate
Molecular Formula: C33H40N2O9.HCl.H2O
Molecular Weight: 663.15
Percent Composition: C 59.77%, H 6.54%, N 4.22%, O 24.13%, Cl 5.35%
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.
Therap-Cat: Antihypertensive.
Therap-Cat-Vet: Hypotensive, tranquilizer. Has been used to prevent aortic rupture in turkeys.
Keywords: Antihypertensive; Reserpine Derivatives.
