Title: Pseudoyohimbine
CAS Registry Number: 84-37-7
CAS Name: (3b,16a,17a)-17-Hydroxyyohimban-16-carboxylic acid methyl ester
Molecular Formula: C21H26N2O3
Molecular Weight: 354.44
Percent Composition: C 71.16%, H 7.39%, N 7.90%, O 13.54%
Literature References: Present in the bark of Corynanthe johimbe K. Schum., Rubiaceae. Obtained from the residues of commercial isoln procedures for the manuf of yohimbine: Karrer, Salomon, Helv. Chim. Acta 9, 1059 (1926). Structure and stereochemistry: Janot et al., Bull. Soc. Chim. Fr. 1952, 1085; 1961, 637. Synthesis: van Tamelen et al., J. Am. Chem. Soc. 80, 5006 (1958); 91, 7315 (1969); Stork, Guthikonda, ibid. 94, 5109 (1972).
Properties: Rhombic platelets, mp 293° (corr, Maquenne block), mp 268° (open capillary), browns at 250°. Also reported as crystals from methanol, mp 252-256° (van Tamelen). [a]D19 +27° (pyridine). uv max (methanol): 225, 281, 290 nm (log e 4.54, 3.86, 3.80).
Melting point: mp 293° (corr, Maquenne block); mp 268° (open capillary); mp 252-256° (van Tamelen)
Optical Rotation: [a]D19 +27° (pyridine)
Absorption maximum: uv max (methanol): 225, 281, 290 nm (log e 4.54, 3.86, 3.80)
Derivative Type: Hydrochloride
Molecular Formula: C21H26N2O3.HCl
Molecular Weight: 390.90
Percent Composition: C 64.52%, H 6.96%, N 7.17%, O 12.28%, Cl 9.07%
Properties: Needles from alcohol + ether, dec 258°. [a]D20 -10° (c = 1 in water).
Optical Rotation: [a]D20 -10° (c = 1 in water)
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