Rescinnamine
Title: Rescinnamine
CAS Registry Number: 24815-24-5
CAS Name: (3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-3,20-yohimban-16-carboxylic acid methyl ester
Additional Names: 3,4,5-trimethoxycinnamic acid ester of methyl reserpate; methyl 3,4,5-trimethoxycinnamoyl reserpate; reserpinine
Trademarks: Cartric (Sanwa); Cinnaloid (Pfizer)
Molecular Formula: C35H42N2O9
Molecular Weight: 634.72
Percent Composition: C 66.23%, H 6.67%, N 4.41%, O 22.69%
Literature References: Found in Rauwolfia serpentina Benth., Apocynaceae: Haack et al., Naturwissenschaften 41, 214 (1954); Ordway, Guercio, US 2876228 (1959 to Pfizer); Klohs et al., US 2974144 (1961 to Riker); from Rauwolfia spp: Banes et al., J. Am. Pharm. Assoc. 47, 625 (1958). Identity with reserpinine: Haack et al., Naturwissenschaften 42, 47 (1955). Structure: Klohs et al., J. Am. Chem. Soc. 77, 2241 (1955). LC-ED determn in urine: J. Wang, M. Bonakdar, J. Chromatogr. 382, 343 (1986). LC determn in rauwolfia preparations: U. R. Cieri, J. AOAC Int. 81, 373 (1998).
Properties: Fine needles from benzene, mp 238-239° (vac). [a]D24 -97° (c = 1 in chloroform). uv max (methanol): 228, 302 nm (log e 4.79, 4.48). Practically insol in water. Moderately sol in methanol, benzene, chloroform, other organic solvents.
Melting point: mp 238-239° (vac)
Optical Rotation: [a]D24 -97° (c = 1 in chloroform)
Absorption maximum: uv max (methanol): 228, 302 nm (log e 4.79, 4.48)
Therap-Cat: Antihypertensive.
Keywords: Antihypertensive; Reserpine Derivatives.

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