8142. Rescinnamine

Nomenclature

CAS number: 24815-24-5
(3β,16β,17α,18β,20α)-11,17-Dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-3,20-yohimban-16-carboxylic acid methyl ester; 3,4,5-trimethoxycinnamic acid ester of methyl reserpate; methyl 3,4,5-trimethoxycinnamoyl reserpate; reserpinine; Cartric (Sanwa); Cinnaloid (Pfizer).
C35H42N2O9; mol wt 634.72.
C 66.23%, H 6.67%, N 4.41%, O 22.69%.

Description and 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).

Chemical structure

Properties

Fine needles from benzene, mp 238-239° (vac). [α]D24 -97° (c = 1 in chloroform). uv max (methanol): 228, 302 nm (log ε 4.79, 4.48). Practically insol in water. Moderately sol in methanol, benzene, chloroform, other organic solvents.

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive; Reserpine Derivatives