8144. Reserpiline
Nomenclature
CAS number: 131-02-2
(3β,19α,20α)-16,17-Didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylic
acid methyl ester. C23H28N2O5; mol wt 412.48.
C 66.97%, H 6.84%, N 6.79%, O 19.39%.
Description and references
Isoln from Rauwolfia serpentina Benth., Apocynaceae: Klohs et al., Chem. Ind. (London) 1954, 1264; from R. canescens L.: Stoll et al., Helv. Chim. Acta 38, 270 (1955). Stereochemistry: Shamma, Richey, J. Am. Chem. Soc. 85, 2507 (1963). Partial synthesis: S.-I. Sakai et al., Heterocycles 17, 99 (1982).
Properties
Amorphous powder. [α]D20 -38° (ethanol); -14° (c = 1.5 in pyridine); -12° (c = 1.7 in chloroform). uv max (ethanol): 229, 300-304 nm (log ε 4.57, 4.03). Freely sol in ethanol, acetone, chloroform, benzene.Derivative
Hydrochloride.C23H28N2O5.HCl; mol wt 448.94.
C 61.53%, H 6.51%, N 6.24%, O 17.82%, Cl 7.90%.
Properties
Crystals, mp 205-207°. [α]D24 -40° (c = 0.44 in ethanol).Derivative
Reserpilic acid dimethylaminoethyl ester dihydrochloride.Nomenclature
CAS number: 3735-84-0
Paratensiol (Yoshitomi); Resporisan (Kowa). C26H35N3O5.2HCl; mol wt 542.50.
C 57.56%, H 6.87%, N 7.75%, O 14.75%, Cl 13.07%.
Therapeutic Category
Antihypertensive.