Deserpidine

Title: Deserpidine
CAS Registry Number: 131-01-1
CAS Name: (3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-3,20-yohimban-16-carboxylic acid methyl ester
Additional Names: 11-desmethoxyreserpine; canescine; recanescine
Trademarks: Harmonyl (Abbott); Raunormine (Penick)
Molecular Formula: C32H38N2O8
Molecular Weight: 578.65
Percent Composition: C 66.42%, H 6.62%, N 4.84%, O 22.12%
Literature 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: a-form, mp 228-232°; b-form, mp 230-232°; and g-form, mp 138° and 226-232° with resolidification at 175°. [a]D20 -163° (c = 0.5 in pyridine). pKa 6.68 in 40% methanol. uv max (ethanol): 218, 272, 290 nm (log e 4.79, 4.26, 4.07).
Melting point: mp 228-232°; mp 230-232°; mp 138° and 226-232° with resolidification at 175°
pKa: pKa 6.68 in 40% methanol
Optical Rotation: [a]D20 -163° (c = 0.5 in pyridine)
Absorption maximum: uv max (ethanol): 218, 272, 290 nm (log e 4.79, 4.26, 4.07)
Derivative Type: Hydrochloride
CAS Registry Number: 6033-69-8
Molecular Formula: C32H38N2O8.HCl
Molecular Weight: 615.11
Percent Composition: 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 Type: Nitrate
Molecular Formula: C32H38N2O8.HNO3
Molecular Weight: 641.67
Percent Composition: C 59.90%, H 6.13%, N 6.55%, O 27.43%
Properties: Crystals, dec 254-260°.
Derivative Type: Oxalate
CAS Registry Number: 119506-01-3
Molecular Formula: C32H38N2O8.C2H2O4
Molecular Weight: 668.69
Percent Composition: C 61.07%, H 6.03%, N 4.19%, O 28.71%
Properties: Crystals, dec 239-243°.
Derivative Type: 10-Methoxydeserpidine
CAS Registry Number: 865-04-3
Additional Names: methoserpidine
Trademarks: Decaserpyl
Molecular Formula: C33H40N2O9
Molecular Weight: 608.68
Percent Composition: C 65.12%, H 6.62%, N 4.60%, O 23.66%
Therap-Cat: Antihypertensive.
Keywords: Antihypertensive; Reserpine Derivatives.
Desflurane Desipramine Deslanoside Desloratadine Deslorelin

Deserpidine
Deserpidine.png
Identifiers
CAS number 131-01-1 YesY
PubChem 8550
ChemSpider 8232 YesY
UNII 9016E3VB47 YesY
DrugBank DB01089
KEGG D08194 YesY
ChEBI CHEBI:27478 YesY
ChEMBL CHEMBL1200515 N
ATC code C02AA05
Jmol-3D images Image 1
Properties
Molecular formula C32H38N2O8
Molar mass 578.65 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Deserpidine is an antihypertensive drug related to reserpine[1] found in Rauvolfia spp.