References of Oxayohimban-16-carboxylicacid, 16,17-didehydro-10-methoxy-19-methyl-, methyl ester, (19a,20a)-
Title: Aricine
CAS Registry Number: 482-91-7
CAS Name: (19a,20a)-16,17-Didehydro-10-methoxy-19-methyloxayohimban-16-carboxylic acid methyl ester
Synonyms: quinovatine; cinchovatine; heterophylline
Molecular Formula: C22H26N2O4
Molecular Weight: 382.45
Percent Composition: C 69.09%, H 6.85%, N 7.32%, O 16.73%
Literature References: Originally found in Cusco bark, the bark of
Cinchona pelletierana Wedd.,
Rubiaceae: Pelletier, Coriol,
J. Pharm. Chim. [2]
15, 565 (1829). Also from
Rauwolfia canescens L.,
R. heterophylla Roem. & Schult.,
R. sellowii Muell. Argov. and
Aspidosperma marcgravianum Woodson.,
Apocynaceae: Stoll
et al., Helv. Chim. Acta 38, 270 (1955); Hochstein
et al., J. Am. Chem. Soc. 77, 3551 (1955); Hochstein,
ibid. 77, 5744 (1955); Gilbert
et al., J. Org. Chem. 27, 4702 (1962). Structure: Stoll
et al., loc. cit. Stereochemistry: Neuss, Boaz,
J. Org. Chem. 22, 1001 (1957); Shamma, Richey,
J. Am. Chem. Soc. 85, 2507 (1963).
Properties: Orthorhombic, elongated prisms from methanol, dec 188°. Sublimes at 0.01 mm and 180°. [a]D20 -91° (c = 1.4 in chloroform); [a]D20 -63° (c = 1.5 in pyridine); [a]D20 -57° (ethanol). uv max (ethanol): 229, 281 nm (log e 4.54, 3.97). pKa in 80% methyl cellosolve 5.80; in 1:1 DMF-water 6.8. Practically insol in water. Sol in 100 parts of 90% alcohol, 33 parts ether. Very sol in chloroform.
pKa: pKa in 80% methyl cellosolve 5.80; in 1:1 DMF-water 6.8
Optical Rotation: [a]D20 -91° (c = 1.4 in chloroform); [a]D20 -63° (c = 1.5 in pyridine); [a]D20 -57° (ethanol)
Absorption maximum: uv max (ethanol): 229, 281 nm (log e 4.54, 3.97)
Derivative Type: Hydrochloride
Molecular Formula: C22H26N2O4.HCl
Molecular Weight: 418.91
Percent Composition: C 63.08%, H 6.50%, N 6.69%, O 15.28%, Cl 8.46%
Properties: Square plates from methanol + acetone, dec 241-254°. [a]D20 -5° (c = 0.9 in 50% ethanol).
Optical Rotation: [a]D20 -5° (c = 0.9 in 50% ethanol)
Derivative Type: Hydrobromide
Molecular Formula: C22H26N2O4.HBr
Molecular Weight: 463.36
Percent Composition: C 57.03%, H 5.87%, N 6.05%, O 13.81%, Br 17.24%
Properties: Needles from methanol, dec 262-263°.
NOTE: Aricine does not seem to share the hypotensive and sedative properties of reserpine: Hochstein
et al., J. Am. Chem. Soc. 77, 3551 (1955).
