2918. Deserpidine
Nomenclature
CAS number: 131-01-1
(3β,16β,17α,18β,20α)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-3,20-yohimban-16-carboxylic
acid methyl ester; 11-desmethoxyreserpine; canescine; recanescine; Harmonyl (Abbott); Raunormine (Penick). C32H38N2O8; mol wt 578.65.
C 66.42%, H 6.62%, N 4.84%, O 22.12%.
Description and references
Isoln from roots of Rauwolfia canescens L., Apocynaceae: A. Stoll, A. Hofmann, J. Am. Chem. Soc. 77, 820 (1955); M. W. Klohs et al., ibid. 4084; N. Neuss et al., ibid. 4087; H. B. MacPhillamy et al., ibid. 4335; E. Schlittler et al., Experientia 11, 64 (1955); GB 791241 (1958 to Penick); GB 809912; P. R. Ulshafer, US 2982769 (1959, 1961 both to Ciba). Stereochemistry: C. F. Huebner et al., Experientia 11, 303 (1955); P. E. Aldrich et al., J. Am. Chem. Soc. 81, 2481 (1959). Synthesis: L. Bláha et al., Collect. Czech. Chem. Commun. 25, 237 (1960); CA 678216 (1964 to Roussel-UCLAF).
Properties
Exists in three cryst forms from methanol: α-form, mp 228-232°; β-form, mp 230-232°; and γ-form, mp 138° and 226-232° with resolidification at 175°. [α]D20 -163° (c = 0.5 in pyridine). pKa 6.68 in 40% methanol. uv max (ethanol): 218, 272, 290 nm (log ε 4.79, 4.26, 4.07).Derivative
Hydrochloride.Nomenclature
CAS number: 6033-69-8
C32H38N2O8.HCl; mol wt 615.11.
C 62.48%, H 6.39%, N 4.55%, O 20.81%, Cl 5.76%.
Properties
Thin rectangular plates from acetone, dec 253-256°.Derivative
Nitrate.C32H38N2O8.HNO3; mol wt 641.67.
C 59.90%, H 6.13%, N 6.55%, O 27.43%.
Properties
Crystals, dec 254-260°.Derivative
Oxalate.Nomenclature
CAS number: 119506-01-3
C32H38N2O8.C2H2O4; mol wt 668.69.
C 61.07%, H 6.03%, N 4.19%, O 28.71%.
Properties
Crystals, dec 239-243°.Derivative
10-Methoxydeserpidine.Nomenclature
CAS number: 865-04-3
methoserpidine; Decaserpyl. C33H40N2O9; mol wt 608.68.
C 65.12%, H 6.62%, N 4.60%, O 23.66%.
Therapeutic Category
Antihypertensive.
Keywords
Antihypertensive; Reserpine Derivatives